Production Method 1

66-99-9

93-09-4

Reaction Conditions

1.1 Reagents: Methanesulfinic acid, 1,1,1-trifluoro-, sodium salt (1:1) ,  Oxygen Solvents: Acetonitrile ;  12 h, 1 atm, rt

Reference

Aerobic oxidation system containing sulfinic acid, sulfonic acid or derivatives thereof and photocatalytic oxidation method therefor

, World Intellectual Property Organization, , ,

Production Method 2

66-99-9

93-09-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Tetramesitylporphyrin Solvents: Acetonitrile ,  Dichloromethane ;  48 h, rt

Reference

A new and efficient aerobic oxidation of aldehydes to carboxylic acids with singlet oxygen in the presence of porphyrin sensitizers and visible light

Hajimohammadi, Mahdi; Safari, Nasser; Mofakham, Hamid; Shaabani, Ahmad, Tetrahedron Letters, 2010, 51(31), 4061-4065

Production Method 3

5773-80-8

93-09-4

Reaction Conditions

1.1 Reagents: Potassium acetate ,  Bis(pinacolato)diborane Catalysts: Palladium Solvents: Ethanol ;  6 h, 60 °C

Reference

Dimerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki-Miyaura Cross-Coupling by One-Pot Synthesis

Du, Fangyu; Zhou, Qifan; Liu, Dongdong; Fang, Ting; Shi, Yajie; et al, Synlett, 2018, 29(6), 779-784

Production Method 4

24091-02-9

93-09-4

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Catalysts: Poly(diseleno-1,2-phenylene) Solvents: Tetrahydrofuran ,  Water
1.2 Reagents: Sodium bicarbonate ,  Sodium chloride Catalysts: Platinum Solvents: Water

Reference

One-pot oxidation of azomethine compounds into arenecarboxylic acids

Giurg, Miroslaw; Said, Samy B.; Syper, Ludwik; Mlochowski, Jacek, Synthetic Communications, 2001, 31(20), 3151-3159

Production Method 5

101482-14-8

93-09-4

Reaction Conditions

1.1 Reagents: Dimethyl sulfoxide Catalysts: Perfluorobutyl iodide ;  27 h, rt

Reference

Preparation method of carboxylic acid compound under photopromotion

, China, , ,

Production Method 6

612-55-5

93-09-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Di-μ-chlorobis(η3-2-propenyl)dipalladium (reaction products with diphenylphosphane and polystyrene-poly(ethylene glycol) resin supported) Solvents: Acetonitrile ,  Water ;  58 s, 5 bar, 100 °C

Reference

Aqueous Flow Hydroxycarbonylation of Aryl Halides Catalyzed by an Amphiphilic Polymer-Supported Palladium-Diphenylphosphine Catalyst

Osako, Takao; Kaiser, Reinhard; Torii, Kaoru; Uozumi, Yasuhiro, Synlett, 2019, 30(8), 961-966

Production Method 7

135-19-3

93-09-4

Reaction Conditions

1.1 Reagents: Triethylamine ,  Sulfonyl fluoride Solvents: Dimethyl sulfoxide ;  2 - 6 h, rt
1.2 Reagents: Sodium bicarbonate ,  Water Catalysts: Palladium diacetate ,  1,3-Bis(diphenylphosphino)propane Solvents: Dimethyl sulfoxide ;  12 h, 60 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1 - 2

Reference

SO2F2-Mediated One-Pot Synthesis of Aryl Carboxylic Acids and Esters from Phenols through a Pd-Catalyzed Insertion of Carbon Monoxide

Fang, Wan-Yin; Leng, Jing; Qin, Hua-Li, Chemistry - An Asian Journal, 2017, 12(17), 2323-2331

Production Method 8

1916516-62-5

93-09-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  11 h, 100 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

Dithioester-enabled chemodivergent synthesis of acids, amides and isothiazoles via C-C bond cleavage and C-O/C-N/C-S bond formations under metal- and catalyst-free conditions

Soni, Sonam; Koley, Suvajit; Singh, Maya Shankar, Tetrahedron Letters, 2017, 58(25), 2512-2516

Production Method 9

76749-35-4

93-09-4

Reaction Conditions

1.1 Reagents: tert-Butyl nitrite Solvents: Water ;  35 min, 29 °C

Reference

tert-Butyl Nitrite-Mediated Synthesis of N-Nitrosoamides, Carboxylic Acids, Benzocoumarins, and Isocoumarins from Amides

Yedage, Subhash L.; Bhanage, Bhalchandra M., Journal of Organic Chemistry, 2017, 82(11), 5769-5781

Production Method 10

19350-74-4

93-09-4

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Catalysts: Poly(diseleno-1,2-phenylene) Solvents: Tetrahydrofuran ,  Water ;  20 h, reflux

Reference

Hydrogen peroxide oxidation of naphthalene derivatives catalyzed by poly(bis-1,2-diphenylene) diselenide

Giurg, M.; Syper, L.; Mlochowski, J., Polish Journal of Chemistry, 2004, 78(2), 231-238

Production Method 11

1592-38-7

93-09-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Catalase ,  Galactose oxidase ,  Aldehyde oxidase Solvents: Acetonitrile ,  Water ;  overnight, pH 7.6, 37 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Enzyme cascade reactions: synthesis of furandicarboxylic acid (FDCA) and carboxylic acids using oxidases in tandem

McKenna, Shane M.; Leimkuhler, Silke; Herter, Susanne; Turner, Nicholas J.; Carnell, Andrew J., Green Chemistry, 2015, 17(6), 3271-3275

Production Method 12

66-99-9

93-09-4

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 13

893-33-4

93-09-4

Reaction Conditions

1.1 Reagents: Sodium bicarbonate ,  Oxygen Catalysts: Tris(2,2′-bipyridyl)ruthenium(II) chloride Solvents: Acetonitrile ;  4 h
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

[Ru(bpy)3]Cl2-catalyzed aerobic oxidative cleavage β-diketones to carboxylic acids under visible light irradiation

Wang, Xiao-Yan; Shang, Zhen-Peng; Zha, Gao-Feng; Chen, Xiao-Qing; Bukhari, Syed Nasir Abbas; et al, Tetrahedron Letters, 2016, 57(50), 5628-5631

Production Method 14

53531-11-6

93-09-4

Reaction Conditions

1.1 Reagents: Boron trifluoride etherate Solvents: Toluene ;  rt → 80 °C; 2 h, 80 °C

Reference

Method for preparing carboxylic acid by removing benzyl protection from benzyl carboxylate

, China, , ,

Production Method 15

1592-38-7

93-09-4

Reaction Conditions

1.1 Solvents: Dichloromethane ;  2 h

Reference

Clean and selective oxidation of aromatic alcohols using silica-supported Jones' reagent in a pressure-driven flow reactor

Wiles, Charlotte; Watts, Paul; Haswell, Stephen J., Tetrahedron Letters, 2006, 47(30), 5261-5264

Production Method 16

19350-74-4

93-09-4

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Catalysts: 2-[[[3-(Trihydroxysilyl)propyl]amino]seleno]benzoyl chloride (silica-supported) Solvents: Tetrahydrofuran ,  Water ;  rt; 50 h, 55 °C
1.2 Reagents: Sodium bicarbonate ,  Sodium chloride Solvents: Water
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Hydroperoxide oxidation of different organic compounds catalyzed by silica-supported selenenamide

Giurg, M.; Brzaszcz, M.; Mlochowski, J., Polish Journal of Chemistry, 2006, 80(3), 417-428

Production Method 17

101482-14-8

93-09-4

Reaction Conditions

1.1 Reagents: Dimethyl sulfoxide ,  Perfluorobutyl iodide ;  27 h, rt

Reference

Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process

Wang, Rui; Xie, Kai-jun; Fu, Qiang; Wu, Min; Pan, Gao-feng; et al, Organic Letters, 2022, 24(10), 2020-2024

Production Method 18

580-13-2

93-09-4

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

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Production Method 19

580-13-2

93-09-4

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 20

93-09-4

Reaction Conditions

1.1 Reagents: Dimethyl sulfide ,  N-Bromosuccinimide ,  4-Hydroxy-2-methoxybenzenemethanol (Polymer supported) Solvents: Dichloromethane
1.2 Reagents: Dimethylacetamide Catalysts: 18-Crown-6
1.3 Reagents: Trifluoroacetic acid Solvents: Dichloromethane

Reference

Efficient synthesis of benzylic bromides under neutral conditions on solid support

Zoller, T.; Ducep, J.-B.; Hibert, M., Tetrahedron Letters, 2000, 41(51), 9985-9988

Production Method 21

93-09-4

80166-90-1

Reaction Conditions

1.1 Reagents: Water Solvents: Dichloromethane ,  1,4-Dioxane

Reference

5-Bromo-7-nitroindoline

Michael, Katja, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007, ,

naphthalene-2-carboxylic acid Raw materials

• 6-Bromo-2-napthoic Acid
• 4,4,4-Trifluoro-3-oxo-2'-butyronaphthone
• 2-naphthaldehyde oxime
• 2-Iodonaphthalene
• 4-methyl-N-(naphthalene-2-ylmethylene)benzenesulfonohydrazide
• Ethyl β-oxo-2-naphthalenepropane(dithioate)
• 2-Bromonaphthalene
• (naphthalen-2-yl)methanol
• Naphthalene-2-carbaldehyde
• N-Methoxy-2-naphthamide
• 2-Naphthalenecarbothioic acid
• benzyl naphthalene-2-carboxylate
• naphthalen-2-ol

naphthalene-2-carboxylic acid Preparation Products

• 5-bromo-7-nitro-indoline (80166-90-1)
• naphthalene-2-carboxylic acid (93-09-4)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Naphthalenecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Naphthalenecarboxylic acids and derivatives Naphthalenecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 40452-20-8(2-Phenanthrenecarboxylicacid)
• 1141-38-4(naphthalene-2,6-dicarboxylic acid)
• 613-08-1(2-Anthracenecarboxylic acid)
• 138308-89-1(Anthracene-2,6-dicarboxylic acid)
• 36428-96-3(pyrene-2-carboxylic acid)
• 2089-89-6(2,7-NDC)
• 1338-14-3(Iron naphthenate)
• 7470-14-6(3-Phenanthrenecarboxylic acid)
• 5774-08-3(2-Naphthalenecarboxylic acid, 6-methyl-)
• 5084-45-7(2-Naphthalenecarboxylic acid, 6-formyl-)