Production Method 1

1916-07-0

884-35-5

Reaction Conditions

1.1 Reagents: Magnesium ,  Iodine Solvents: Diethyl ether ;  0 °C; 2 h, reflux
1.2 Solvents: Dichloromethane ;  1 h, 80 °C
1.3 Reagents: Sodium thiosulfate Solvents: Ethyl acetate ,  Water

Reference

A synthetic approach to chrysophaentin F

Vendeville, Jean-Baptiste; et al, Chemical Communications (Cambridge, 2019, 55(33), 4837-4840

Production Method 2

530-57-4

884-35-5

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol ,  Water ;  rt → reflux; 3 h, reflux

Reference

Reactions of 2,2-diphenyl-1-picrylhydrazyl (DPPH) with two syringylic phenols or one aroxide derivative

Hristea, Elena N.; et al, European Journal of Organic Chemistry, 2009, (5), 626-634

Production Method 3

27065-65-2

884-35-5

Reaction Conditions

1.1 Reagents: Nickel dichloride ,  Sodium borohydride Solvents: Methanol ;  5 - 10 min, 0 °C
1.2 Reagents: Methanol ;  20 min

Reference

NiCl2·6H2O/NaBH4 in methanol: a mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers

Chouhan, Mangilal; et al, Tetrahedron Letters, 2013, 54(34), 4540-4543

Production Method 4

1147-85-9

884-35-5

Reaction Conditions

1.1 Reagents: Nickel dichloride ,  Sodium borohydride Solvents: Methanol ;  5 - 10 min, 0 °C
1.2 Reagents: Methanol ;  20 min

Reference

NiCl2·6H2O/NaBH4 in methanol: a mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers

Chouhan, Mangilal; et al, Tetrahedron Letters, 2013, 54(34), 4540-4543

Production Method 5

149-91-7

884-35-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  1 h, reflux

Reference

Design and synthesis of a series of serine derivatives as small molecule inhibitors of the SARS coronavirus 3CL protease

Konno, Hiroyuki; et al, Bioorganic & Medicinal Chemistry, 2016, 24(6), 1241-1254

Production Method 6

91-10-1

884-35-5

Reaction Conditions

1.1 Catalysts: 1,10-Phenanthroline Solvents: Methanol ;  36 h, 120 °C

Reference

Nickel-catalyzed para-selective carboxylation of phenols with CBr4/MeOH

Tu, Guangliang; et al, Organic Chemistry Frontiers, 2022, 9(14), 3876-3881

Production Method 7

118-41-2

884-35-5

Reaction Conditions

1.1 Reagents: Boron trichloride Solvents: Dichloromethane ;  -10 °C; 30 h, -10 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Synthesis of leptosin, a glycoside isolated from manuka honey

Aitken, Harry R. M.; et al, Tetrahedron Letters, 2013, 54(50), 6916-6919

Production Method 8

149-91-7

884-35-5

Reaction Conditions

1.1 Catalysts: Sulfuric acid
1.2 Reagents: Dimethyl sulfate
2.1 Reagents: Zinc chloride Solvents: Propionic acid

Reference

Novel selective demethylation reaction-synthesis of 3,5- dimethoxy-4-hydroxybenzoate

Jing, Xiaobi; et al, Lanzhou Daxue Xuebao, 2001, 37(3), 78-79

Production Method 9

149-91-7

884-35-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  4 h, reflux
2.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  4 h, rt

Reference

Synthesis of diverse analogues of Oenostacin and their antibacterial activities

Srivastava, Vandana; et al, Bioorganic & Medicinal Chemistry, 2007, 15(1), 518-525

Production Method 10

530-57-4

884-35-5

Reaction Conditions

1.1 Reagents: Thionyl chloride Catalysts: Pyridine Solvents: Diethyl ether ;  2 - 4 h, 80 °C
2.1 Solvents: Diethyl ether ;  8 - 10 h, 70 - 80 °C

Reference

Phenolic acid derivatives as preservatives: synthesis, antioxidant, antimicrobial potential and their preservative effectiveness

Sigroha, Sumit; et al, International Journal of Pharmaceutical Sciences and Research, 2021, 12(10), 5526-5537

Production Method 11

1916-07-0

884-35-5

Reaction Conditions

1.1 Reagents: Boron trichloride

Reference

Boron trichloride as a selective demethylating agent for hindered ethers

Carvalho, Christopher F.; et al, Journal of the Chemical Society, 1984, (4), 227-9

Production Method 12

530-57-4

884-35-5

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Methanol ;  6 h, reflux

Reference

Synthesis and Antileukemic Activities of Piperlongumine and HDAC Inhibitor Hybrids against Acute Myeloid Leukemia Cells

Liao, Yi; et al, Journal of Medicinal Chemistry, 2016, 59(17), 7974-7990

Production Method 13

530-57-4

884-35-5

Reaction Conditions

1.1 Reagents: 1,8-Bis(tetramethylguanidino)naphthalene Solvents: Dimethylformamide ;  rt
1.2 Reagents: Formic acid Solvents: Water

Reference

Alkylation of carboxylic acids in a microfluidic device: kinetics parameters determination, Hammett reaction constant measurement and optimization of preparative experiment

Gholamipour-Shirazi, Azarmidokht; et al, International Electronic Conference on Synthetic Organic Chemistry, 2009, ,

Production Method 14

27065-65-2

884-35-5

Reaction Conditions

Reference

Product class 8: ethers as protecting groups

Petursson, S., Science of Synthesis, 2008, 37, 847-892

Production Method 15

130774-07-1

884-35-5

Reaction Conditions

Reference

Studies on the constituents of the bark of Kalopanax pictus Nakai

Sano, Kazuko; et al, Chemical & Pharmaceutical Bulletin, 1991, 39(4), 865-70

Production Method 16

134-96-3

884-35-5

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Alumina ,  Gold ;  0.3 MPa, rt; 4 h, 140 °C

Reference

Gold-mediated selective transformation of lignin models to aromatic esters in the presence of molecular oxygen

Zhuang, Xuli; et al, Catalysis Today, 2017, 298, 190-196

Production Method 17

50597-60-9

884-35-5

Reaction Conditions

1.1 Solvents: Diethyl ether ;  8 - 10 h, 70 - 80 °C

Reference

Phenolic acid derivatives as preservatives: synthesis, antioxidant, antimicrobial potential and their preservative effectiveness

Sigroha, Sumit; et al, International Journal of Pharmaceutical Sciences and Research, 2021, 12(10), 5526-5537

Production Method 18

91925-82-5

884-35-5

Reaction Conditions

1.1 Reagents: Potassium carbonate
1.2 Reagents: Hydrogen Catalysts: Palladium

Reference

Synthesis and antioxidant activities of 3,5-dialkoxy-4-hydroxycinnamamides

Kang, Tae-Souk; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(5), 1663-1667

Production Method 19

91925-82-5

884-35-5

Reaction Conditions

Reference

Product class 8: ethers as protecting groups

Petursson, S., Science of Synthesis, 2008, 37, 847-892

Production Method 20

99-24-1

884-35-5

Reaction Conditions

Reference

Product class 8: ethers as protecting groups

Petursson, S., Science of Synthesis, 2008, 37, 847-892

Production Method 21

782452-40-8

884-35-5

530-57-4

Reaction Conditions

1.1 Reagents: Ethylene glycol Solvents: Ethylene glycol ;  1 h, 120 °C

Reference

Simple deprotection of acetal type protecting groups under neutral conditions

Miyake, Hideyoshi; et al, Tetrahedron Letters, 2004, 45(39), 7213-7215

Production Method 22

1916-07-0

884-35-5

3934-86-9

Reaction Conditions

1.1 Reagents: Methanesulfonic acid ;  48 h, 60 °C

Reference

Regioselective demethylation catalyzed by methylsulfonic acid

Zhang, Cheng-gang, Sichuan Shifan Daxue Xuebao, 2004, 27(5), 523-524

methyl 4-hydroxy-3,5-dimethoxy-benzoate Raw materials

• Methyl 3,4,5-trimethoxybenzoate
• Methyl 4-(benzyloxy)-3,5-dimethoxybenzoate
• Benzoyl chloride, 4-hydroxy-3,5-dimethoxy-
• Methyl syringate 4-O-alpha-L-rhamnopyranoside
• Gallic acid
• Methyl 4-(benzyloxy)-3,5-dihydroxybenzoate
• Syringaldehyde
• Syringic acid
• 2,6-Dimethoxyphenol
• Benzoic acid, 3,5-dimethoxy-4-(2-propen-1-yloxy)-, methyl ester
• Benzoic acid, 3,5-dimethoxy-4-(methoxymethoxy)-, methyl ester
• 3,4,5-Trimethoxybenzoic acid
• Methyl gallate

methyl 4-hydroxy-3,5-dimethoxy-benzoate Preparation Products

• Syringic acid (530-57-4)
• methyl 4-hydroxy-3,5-dimethoxy-benzoate (884-35-5)
• Methyl 3-O-methylgallate (3934-86-9)

• 1. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 2. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
  Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651
• 3. Excitation energies from ground-state density-functionals by means of generator coordinates
  A. B. F. da Silva,K. Capelle Phys. Chem. Chem. Phys., 2009,11, 4564-4569
• 4. Fast-pulsing NMR techniques for the detection of weak interactions: successful natural abundance probe of hydrogen bonds in peptides?
  Amandine Altmayer-Henzien,Valérie Declerck,David J. Aitken,Ewen Lescop,Denis Merlet,Jonathan Farjon Org. Biomol. Chem., 2013,11, 7611-7615
• 5. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Gallic acid and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

• 2150-38-1(Methyl 3,4-dimethoxybenzoate)
• 1916-07-0(Methyl 3,4,5-trimethoxybenzoate)
• 1182838-07-8(Methyl 3,4,5-Trimethoxy-d9-benzoate)
• 1189921-34-3(Methyl 3,4-Dimethoxy7-13C-benzoate)
• 91925-82-5(Methyl 4-(benzyloxy)-3,5-dihydroxybenzoate)
• 83011-43-2(Methyl 3-hydroxy-4,5-dimethoxybenzoate)
• 6702-50-7(Methyl isovanillate)
• 3943-74-6(Methyl vanillate)
• 3934-86-9(Methyl 3-O-methylgallate)
• 70424-94-1(Methyl 3,4,5-Tris(benzyloxy)benzoate)