Production Method 1

97-54-1

97-53-0

Reaction Conditions

1.1 Catalysts: Dichlorotris(triphenylphosphine)ruthenium ;  rt → 60 °C; 4 h, 60 °C

Reference

Preparation of vanillin from eugenol

, China, , ,

Production Method 2

151276-06-1

97-53-0

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Tetrabutylammonium bromide ,  Palladium ;  90 min, 100 °C

Reference

Application of a new phosphorus-free palladium heterogeneous nanocatalyst supported on modified MWCNT the highly selective and efficient cleavage of propargyl, allyl, and benzyl phenol ethers under mild conditions

Sharghi, Hashem; Khoshnood, Abbas; Khalifeh, Reza; Doroodmand, Mohammad Mehdi, Molecular Diversity, 2015, 19(3), 481-500

Production Method 3

97-53-0

Reaction Conditions

1.1 Reagents: Acetyl bromide Catalysts: Lithium bromide ;  6 h, 30 - 35 °C
1.2 Reagents: Methanol ;  0.75 - 4 h, rt

Reference

Process for the preparation of alcohol by dealkylation of alkyl ethers with acyl halide in the presence of a catalytic system

, India, , ,

Production Method 4

97-53-0

Reaction Conditions

1.1 Catalysts: 1,5-Diazabicyclo[4.3.0]non-5-ene Solvents: Decane

Reference

Preparation of phenyl alkyl (thio)ethers

, Germany, , ,

Production Method 5

2216-99-1

97-53-0

Reaction Conditions

1.1 Reagents: Lithium chloride Solvents: N,N-Dimethylaniline ;  rt → 190 °C; 3 h, 190 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  1 h, 25 °C

Reference

Method for synthesizing para-eugenol

, World Intellectual Property Organization, , ,

Production Method 6

97-53-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide ,  1,1,3,3-Tetramethyldisiloxane ,  Manganese Catalysts: Dibromo[1,2-di(methoxy-κO)ethane]nickel ,  1H-Imidazolium, 1,3-dicyclohexyl-, tetrafluoroborate(1-) (1:1) Solvents: Toluene ;  5 h, 70 °C
1.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  2 h, 70 °C

Reference

Nickel-Catalyzed Reductive Deoxygenation of Diverse C-O Bond-Bearing Functional Groups

Cook, Adam; MacLean, Haydn; St. Onge, Piers; Newman, Stephen G., ACS Catalysis, 2021, 11(21), 13337-13347

Production Method 7

6331-61-9

97-53-0

Reaction Conditions

1.1 Reagents: Triethylamine ,  Phosphorazidic acid, diethyl ester Solvents: Dimethylformamide ,  Toluene ;  30 min, rt; 3 h, reflux
1.2 Reagents: Potassium hydroxide Solvents: Glycerol ,  Ethanol ,  Water ;  2 h, reflux
1.3 Reagents: Citric acid Solvents: Water ;  pH 5

Reference

High-yielding cleavage of (aryloxy) acetates

Spurg, Anke; Waldvogel, Siegfried R., European Journal of Organic Chemistry, 2008, (2), 337-342

Production Method 8

127393-84-4

97-53-0

Reaction Conditions

1.1 Reagents: Nickel dichloride Solvents: Methanol
1.2 Reagents: Sodium borohydride

Reference

Deoxymercuration with nickel boride

Singhal, G. M.; Sarma, J. C.; Sharma, R. P., Indian Journal of Chemistry, 1989, (1989), 853-4

Production Method 9

8068-05-1

97-53-0

2380-78-1

93-51-6

97-54-1

90-05-1

2785-89-9

306-08-1

127473-64-7

Reaction Conditions

1.1 Catalysts: Silica Solvents: Ethanol ;  4 h, 290 °C

Reference

Catalytic depolymerization of Kraft lignin to high yield alkylated-phenols over CoMo/SBA-15 catalyst in supercritical ethanol

Rana, Masud; et al, RSC Advances, 2023, 13(43), 30022-30039

Production Method 10

370085-78-2

97-53-0

Reaction Conditions

1.1 Reagents: Water Solvents: Methyl ethyl ketone ;  200 h, 20 °C

Reference

Esterification study of acetoxysilane by alcohols and phenols

Kopylov, Victor; Ivanov, Vladimir; Zheneva, Marina; Kireev, Vyacheslav; Djakov, Valerii, Organosilicon Chemistry V: Molecules to Materials, 2003, (2003), 344-347

Production Method 11

370085-78-2

97-53-0

Reaction Conditions

1.1 Reagents: Silica ,  Oxygen ;  20 h, 20 °C; 10 h, 100 °C

Reference

Silicone derivatives of fragrant, flavoring and medicinal substances

, World Intellectual Property Organization, , ,

Production Method 12

2463612-06-6

97-53-0

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid monohydrate Solvents: Dichloromethane ;  rt

Reference

Preparation of eugenol

, China, , ,

Production Method 13

4125-45-5

97-53-0

Reaction Conditions

1.1 Reagents: tert-Butyllithium Solvents: Diethyl ether ,  Pentane ;  -78 °C; 2 h, -78 °C
1.2 Reagents: Methanol ;  -78 °C; -78 °C → rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Selective O-deallylation of ortho-allyloxyanisoles

Sanz, Roberto; Martinez, Alberto; Marcos, Cesar; Fananas, Francisco J., Synlett, 2008, (13), 1957-1960

Production Method 14

151276-06-1

97-53-0

Reaction Conditions

1.1 Reagents: Magnesium ,  Titanium chloride (TiCl3) Solvents: Tetrahydrofuran

Reference

Selective deprotection of ethers by low-valent titanium: facile cleavage of propargyl ethers

Nayak, Sandip K.; Kadam, Suresh M.; Banerji, Asoke, Synlett, 1993, (8), 581-2

Production Method 15

93-28-7

97-53-0

Reaction Conditions

1.1 Catalysts: Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Methanol ;  1 - 12 h, rt

Reference

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot

Gurawa, Aakanksha; Kumar, Manoj; Rao, Dodla S.; Kashyap, Sudhir, New Journal of Chemistry, 2020, 44(39), 16702-16707

Production Method 16

143654-03-9

97-53-0

Reaction Conditions

1.1 Reagents: Bismuth trichloride Solvents: Acetonitrile ,  Water ;  1 h, 50 °C

Reference

Bismuth trichloride-mediated cleavage of phenolic methoxymethyl ethers

Obaro-Best, Oghale; Reed, Jack; Norfadilah, Alya A. F. B.; Monahan, Ryan; Sunasee, Rajesh, Synthetic Communications, 2016, 46(7), 586-593

Production Method 17

90-05-1

97-53-0

Reaction Conditions

1.1 Catalysts: Cupric nitrate ,  Cobalt dinitrate Solvents: Water ;  rt → 75 °C; 75 °C → rt
1.2 Catalysts: Urea ;  12 h, 200 °C; 900 °C
1.3 Catalysts: Ethylenediaminetetraacetic acid ,  (+)-Tartaric acid
1.4 Reagents: Ammonium hydroxide Solvents: Water ;  pH 11
1.5 Reagents: Sodium hydroxide Solvents: Water ;  rt; rt → 16 °C
1.6 Reagents: Sodium chloride Solvents: Water ;  16 °C; 16 °C → 12 °C
1.7 2 h, 22 °C; 1 h, 27 °C

Reference

A method for synthesis of eugenol

, China, , ,

Production Method 18

214330-24-2

97-53-0

Reaction Conditions

1.1 Catalysts: Sodium tetrachloroaurate Solvents: Methanol ;  7 h, rt

Reference

Mild and Selective Deprotection of tert-Butyl(dimethyl)silyl Ethers with Catalytic Amounts of Sodium Tetrachloroaurate(III) Dihydrate

Zhang, Qi; Kang, Xiuqin; Long, Lei; Zhu, Lijuan; Chai, Yonghai, Synthesis, 2015, 47(1), 55-64

Production Method 19

93-28-7

97-53-0

Reaction Conditions

1.1 Reagents: Potassium iodide ,  Aluminum trichloride hexahydrate Solvents: Acetonitrile ,  Water ;  30 min, rt
1.2 4 h, 80 °C

Reference

AlCl3.6H2O/KI/CH3CN/H2O. An efficient and versatile system for chemoselective C-O bond cleavage and formation of halides and carbonyl compounds from alcohols in hydrated media

Gogoi, Pranjal; Konwar, Dilip; Das Sharma, Saikat; Gogoi, Prodip Kumar, Synthetic Communications, 2006, 36(9), 1259-1264

Production Method 20

108-31-6

97-53-0

97-53-0

Reaction Conditions

1.1 Catalysts: Hydrochloric acid Solvents: Acetone ,  Water ;  80 °C

Reference

Study on characterization and degree of esterification of styrene maleic anhydride by some medicines

Rajput, Ravish Singh; Rupainwar, D. C.; Singh, Rama Kant; Singh, Amarika, Indian Journal of Chemistry, 2009, (2009), 1597-1600

Eugenol Raw materials

• Isoeugenol
• Guaiacol
• (4-Allyl-2-methoxyphenoxy)acetic acid
• Sulfate Lignin
• 5-Allyl-2-hydroxy-3-methoxybenzoic acid
• Silanediol, [2-methoxy-4-(2-propenyl)phenoxy]methyl-, diacetate
• 1-(2-Ethoxyethoxy)-2-methoxy-4-(2-propen-1-yl)benzene
• Mercury, bromo[3-(4-hydroxy-3-methoxyphenyl)-2-methoxypropyl]-
• Benzene, 2-methoxy-4-(2-propenyl)-1-(2-propenyloxy)-
• 2,5-dihydrofuran-2,5-dione
• Eugenol acetate
• Eugenol
• 4-allyl-2-methoxy-1-(methoxymethoxy)benzene
• BENZENE, 2-METHOXY-4-(2-PROPENYL)-1-(2-PROPYNYLOXY)-
• Silane, (1,1-dimethylethyl)[2-methoxy-4-(2-propenyl)phenoxy]dimethyl-

Eugenol Preparation Products

• Homovanillyl alcohol (2380-78-1)
• 2-Methoxy-4-methylphenol (93-51-6)
• Isoeugenol (97-54-1)
• Guaiacol (90-05-1)
• 4-Ethylguaiacol (2785-89-9)
• Eugenol (97-53-0)
• 4-Hydroxy-3-methoxyphenylacetic Acid (306-08-1)
• 2(1H)-Pyrimidinone,5-(1-methylpropyl)-, (S)- (9CI) (127473-64-7)

• 1. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466
• 2. Evidence of rutile-to-anatase photo-induced electron transfer in mixed-phase TiO2 by solid-state NMR spectroscopy?
  Weili Dai,Guangjun Wu,Michael Hunger Chem. Commun., 2015,51, 13779-13782
• 3. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
  Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212
• 4. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592
• 5. Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy?
  Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia Chen Phys. Chem. Chem. Phys., 2017,19, 25471-25477

• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols Methoxyphenols
• Natural Products and Extracts Plant Extracts Plant based Rhanterium epapposum
• Natural Products and Extracts Plant Extracts Plant based Laser trilobum

• 487-11-6(Elemicin)
• 18738-93-7(Benzene,2-methoxy-1-phenoxy-4-(2-propen-1-yl)-)
• 62416-75-5(Benzene, 1,2-diethoxy-4-(2-propenyl)-)
• 8068-83-5(N 2)
• 85187-52-6(Piperidine,[(tetrahydro-2-furanyl)methyl]- (9CI))
• 32601-56-2(Phenol, 2-methoxy-4-(2-propen-1-yl)-, zinc salt (2:1))
• 83864-78-2(Obovatol)
• 93-15-2(Methyl Eugenol)
• 6627-88-9(4-allyl-2,6-dimethoxyphenol)
• 62486-66-2(Benzene, 4-(2-butenyl)-1,2-dimethoxy-, (E)-)