Production Method 1

94-53-1

Reaction Conditions

1.1 Reagents: Monosodium phosphate ,  Hydrogen peroxide ,  Sodium chlorite Solvents: Acetonitrile ,  Water ;  2 h, 15 °C

Reference

Convergent Synthesis of Pancratistatin from Piperonal and Xylose

Dam, Johan Hygum; Madsen, Robert, European Journal of Organic Chemistry, 2009, (27), 4666-4673

Production Method 2

495-76-1

94-53-1

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Benzyltrimethylammonium tribromide Solvents: Water

Reference

Oxidation using quaternary ammonium polyhalides. V. Selective oxidation of benzyl alcohols by the use of benzyltrimethylammonium tribromide

Okamoto, Tsuyoshi; Uesugi, Takeshi; Kakinami, Takaaki; Utsunomiya, Tomohisa; Kajigaeshi, Shoji, Bulletin of the Chemical Society of Japan, 1989, 62(11), 3748-9

Production Method 3

94-53-1

Reaction Conditions

1.1 Reagents: 1-Hydroxycyclohexyl phenyl ketone ,  Sodium hydroxide Solvents: 1,2-Dimethoxyethane ;  80 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  neutralized

Reference

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

Tan, Wen-Yun; Lu, Yi; Zhao, Jing-Feng; Chen, Wen; Zhang, Hongbin, Organic Letters, 2021, 23(17), 6648-6653

Production Method 4

495-76-1

94-53-1

Reaction Conditions

1.1 Catalysts: Potassium carbonate ,  Platinum Solvents: Water ;  80 °C

Reference

Platinum nanoparticles supported on polymeric ionic liquid functionalized magnetic silica: effective and reusable heterogeneous catalysts for the selective oxidation of alcohols in water

Vessally, Esmail; Ghasemisarabbadeih, Mostafa; Ekhteyari, Zeynab; Hosseinzadeh-Khanmiri, Rahim; Ghorbani-Kalhor, Ebrahim; et al, RSC Advances, 2016, 6(108), 106769-106777

Production Method 5

94-53-1

Reaction Conditions

1.1 Reagents: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene ,  Oxygen Catalysts: 5H-Pyrrolo[2,1-c]-1,2,4-triazolium, 6,7-dihydro-2-(2,4,6-trimethylphenyl)-, tetr… Solvents: Acetonitrile ;  1 - 24 h, rt

Reference

Cooperative N-heterocyclic carbene (NHC) and ruthenium redox catalysis: Oxidative esterification of aldehydes with air as the terminal oxidant

Zhao, Junfeng; Mueck-Lichtenfeld, Christian; Studer, Armido, Advanced Synthesis & Catalysis, 2013, 355(6), 1098-1106

Production Method 6

2635-13-4

94-53-1

Reaction Conditions

1.1 Reagents: Poly(methylhydrosiloxane) Catalysts: Cupric acetate ,  1,2-Bis(diphenylphosphino)benzene Solvents: 1,4-Dioxane ;  25 min, 60 °C
1.2 Reagents: Triethylamine Catalysts: Palladium diacetate ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Toluene ;  3 h, 100 °C; 100 °C → rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  10 min, rt
1.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 1 - 2

Reference

Method for preparing aromatic carboxylic acid compound

, China, , ,

Production Method 7

2635-13-4

94-53-1

Reaction Conditions

1.1 Reagents: Poly(methylhydrosiloxane) Catalysts: Cupric acetate ,  1,2-Bis(diphenylphosphino)benzene Solvents: 1,4-Dioxane ;  20 min, rt → 65 °C
1.2 Reagents: Triethylamine Catalysts: Palladium diacetate ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Toluene ;  3 h, rt → 100 °C; 100 °C → rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  10 min, rt

Reference

Tandem one-pot CO2 reduction by PMHS and silyloxycarbonylation of aryl/vinyl halides to access carboxylic acids

Paridala, Kumaraswamy; Lu, Sheng-Mei; Wang, Meng-Meng; Li, Can, Chemical Communications (Cambridge, 2018, 54(82), 11574-11577

Production Method 8

495-76-1

94-53-1

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Catalysts: Poly(oxy-1,2-ethanediyl), α-[2-[1-(3-sulfopropyl)-1H-imidazolium-3-yl]ethyl]-ω-[… Solvents: Toluene ,  Water ;  rt; 4 h, 85 °C

Reference

PEG1000-DAIL/toluene temperature-dependent biphasic system that regulate homogeneously catalyzed oxidation of primary alcohols to carboxylic acids

Hu, Yu Lin; Ma, Xiao Yun; Ge, Qiang; Lu, Ming, Acta Chimica Slovenica, 2010, 57(4), 927-930

Production Method 9

94-53-1

Reaction Conditions

1.1 Solvents: Water ;  30 °C
1.2 Reagents: Sulfuric acid ;  pH 2

Reference

Biotransformations of propenylbenzenes by an Arthrobacter sp. and its t-anethole blocked mutants

Shimoni, Eyal; Baasov, Timor; Ravid, Uzi; Shoham, Yuval, Journal of Biotechnology, 2003, 105, 61-70

Production Method 10

141-97-9

94839-07-3

94-53-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Cuprous iodide Solvents: Dimethyl sulfoxide ;  24 h, 100 °C; cooled
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Copper-catalyzed synthesis of aromatic carboxylic acids from arylboronic acids and acetyl acetate

Zheng, Rui; Zhou, Qizhong; Gu, Haining; Jiang, Huajiang; Wu, Jiashou; et al, Tetrahedron Letters, 2014, 55(41), 5671-5675

Production Method 11

14874-70-5

45891-56-3

94-53-1

Reaction Conditions

1.1 Reagents: Water Catalysts: Tris(2,2′-bipyridyl)ruthenium(II) chloride Solvents: Acetonitrile ;  3 h, 10 bar, rt

Reference

Visible-Light-Mediated Hydroxycarbonylation of Diazonium Salts

Gosset, Cyrille; Pellegrini, Sylvain; Jooris, Romain; Bousquet, Till; Pelinski, Lydie, Advanced Synthesis & Catalysis, 2018, 360(17), 3401-3405

Production Method 12

495-76-1

94-53-1

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Potassium chloride ,  1-Butanaminium, N,N,N-tributyl-, ferratehexa-μ3-hydroxyhexa-μ-oxododecaoxohexamo… Solvents: Water ;  24 h, 1 atm, 70 °C

Reference

Selective iron-catalyzed aerobic oxidation of alcohols in water to carboxylic acids mediated by additives

Yu, Han; Ren, Jingjing; Xie, Ya; Su, Xiaofang; Wang, Aiping; et al, Green Chemistry, 2022, 24(17), 6511-6516

Production Method 13

94-53-1

Reaction Conditions

1.1 Reagents: Sodium carbonate ,  Oxygen Catalysts: Molybdate(4-), cupratehexa-μ3-hydroxyhexa-μ-oxododecaoxohexa-, ammonium (1:4) Solvents: Water ;  12 h, 50 °C

Reference

An Efficient Aerobic Oxidation Protocol of Aldehydes to Carboxylic Acids in Water Catalyzed by an Inorganic-Ligand-Supported Copper Catalyst

Yu, Han; Ru, Shi; Zhai, Yongyan; Dai, Guoyong; Han, Sheng; et al, ChemCatChem, 2018, 10(6), 1253-1257

Production Method 14

551906-15-1

94-53-1

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran ,  Water ;  rt; 12 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt

Reference

Accessing N-Acyl Azoles via Oxoammonium Salt-Mediated Oxidative Amidation

Ovian, John M.; Kelly, Christopher B. ; Pistritto, Vincent A.; Leadbeater, Nicholas E., Organic Letters, 2017, 19(6), 1286-1289

Production Method 15

495-76-1

94-53-1

Reaction Conditions

1.1 Reagents: 1-Hydroxycyclohexyl phenyl ketone ,  Sodium hydroxide Solvents: 1,2-Dimethoxyethane ;  80 °C; 80 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt

Reference

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids with 1-Hydroxycyclohexyl Phenyl Ketone

Lu, Yi; Tan, Wen-Yun; Ding, Yuzhen; Chen, Wen ; Zhang, Hongbin, Journal of Organic Chemistry, 2023, 88(13), 8114-8122

Production Method 16

94-53-1

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Permanganic acid (HMnO4), potassium salt (1:1) Catalysts: Tetramethylammonium bromide Solvents: Water ;  pH 9, 25 - 30 °C; 30 °C → 45 °C; 3 h, 40 - 45 °C

Reference

Method for preparation of piperonylic acid with heliotropine by phase transfer catalysis oxidation

, China, , ,

Production Method 17

94-53-1

Reaction Conditions

1.1 Reagents: 2-Methyl-2-butene ,  Sodium phosphate ,  Sodium chlorite Solvents: tert-Butanol ,  Water ;  2 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water
1.3 Reagents: Hydrochloric acid Solvents: Water

Reference

A Domino Amidation Route to Indolines and Indoles: Rapid Syntheses of Anhydrolycorinone, Hippadine, Oxoassoanine, and Pratosine

Ganton, Michael D.; Kerr, Michael A., Organic Letters, 2005, 7(21), 4777-4779

Production Method 18

7145-99-5

94-53-1

Reaction Conditions

1.1 Reagents: Potassium persulfate ,  Oxygen Catalysts: Molybdate(3-), chromatehexa-μ3-hydroxyhexa-μ-oxododecaoxohexa-, ammonium (1:3) Solvents: Water ;  24 h, 50 °C

Reference

An efficient chromium(III)-catalyzed aerobic oxidation of methylarenes in water for the green preparation of corresponding acids

Jiang, Feng; Liu, Shanshan; Zhao, Wenshu; Yu, Han; Yan, Likai; et al, Dalton Transactions, 2021, 50(36), 12413-12418

Production Method 19

495-76-1

94-53-1

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: 2069173-90-4 Solvents: Toluene ;  12 h, 120 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

Acceptorless dehydrogenation of primary alcohols to carboxylic acids by self-supported NHC-Ru single-site catalysts

Yin, Shenxiang; Zheng, Qingshu; Chen, Jie; Tu, Tao, Journal of Catalysis, 2022, 408, 165-172

Production Method 20

94-53-1

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Dipropylene glycol dimethyl ether ;  rt; 10 h, 80 °C

Reference

Green and Efficient: Oxidation of Aldehydes to Carboxylic Acids and Acid Anhydrides with Air

Liu, Kai-Jian; Fu, Yu-Ling; Xie, Long-Yong; Wu, Chao; He, Wei-Bao; et al, ACS Sustainable Chemistry & Engineering, 2018, 6(4), 4916-4921

Piperonylic acid Raw materials

• Piperonyl alcohol
• 4-Bromo-1,2-methylenedioxybenzene
• Ethyl acetoacetate
• (2H-1,3-benzodioxol-5-yl)boronic acid
• Borate(1-),tetrafluoro-
• 1,3-Benzodioxol-5-yl-1H-pyrazol-1-ylmethanone
• 1,3-Benzodioxole-5-diazonium
• 5-Methyl-1,3-benzodioxole

Piperonylic acid Preparation Products

• Piperonylic acid (94-53-1)

• 1. An ion-gating multinanochannel system based on a copper-responsive self-cleaving DNAzyme?
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• 2. An ion-exchange method for determining paraquat residues in food crops
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  Analyst, 1966,91, 208-210
• 5. An antioxidant self-healing hydrogel for 3D cell cultures?
  Lei Yang,Yuan Zeng,Haibo Wu,Chunwu Zhou,Lei Tao J. Mater. Chem. B, 2020,8, 1383-1388

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzodioxoles Benzodioxoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzodioxoles
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 35142-05-3(aristolic acid)
• 24351-56-2(3',4'-(Methylenedioxy)-3-biphenylcarboxylic Acid)
• 526-34-1(7-methoxy-1,3-dioxaindane-5-carboxylic acid)
• 326-56-7(methyl 2H-1,3-benzodioxole-5-carboxylate)
• 1261960-47-7(5-Methoxy-3-(3,4-methylenedioxyphenyl)benzoic acid)
• 1258628-34-0(5-Hydroxy-3-(3,4-methylenedioxyphenyl)benzoic acid)
• 482627-94-1(7-hydroxy-1,3-benzodioxole-5-carboxylic acid)
• 5025-54-7(6-methyl-1,3-dioxaindane-5-carboxylic acid)
• 193151-97-2(4-Biphenyl-1,3Dioxol-5-Yl-Carboxylic Acid)
• 56359-06-9(1,3-Benzodioxole-5-carboxylic acid, sodium salt (1:1))