2,5-dihydroxy-4-methylbenzoic acid methyl ester

Base Information

• Chemical Name: 2,5-dihydroxy-4-methylbenzoic acid methyl ester
• CAS No.: 3899-19-2
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.176
• Mol file: 3899-19-2.mol

Synonyms:2,5-dihydroxy-4-methylbenzoic acid methyl ester

Chemical Property of 2,5-dihydroxy-4-methylbenzoic acid methyl ester

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-dihydroxy-4-methylbenzoic acid methyl ester

There total 7 articles about 2,5-dihydroxy-4-methylbenzoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 2-bromo-5-methylbenzene-1,4-diol (67289-05-8) → 2,5-dihydroxy-4-methylbenzoic acid methyl ester (3899-19-2)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tributyl-amine; In N,N-dimethyl-formamide; at 110 ℃; for 30h; under 21720.2 Torr;

DOI:10.1021/ja0367602

Reference yield:

2-Methyl-1,4-benzoquinone (553-97-9) → 2,5-dihydroxy-4-methylbenzoic acid methyl ester (3899-19-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / TMSBr; Bu₄NBF₄ / acetonitrile

2: 67 percent / Pd(dppf)Cl₂*CH₂Cl₂; Bu₃N / dimethylformamide / 30 h / 110 °C / 21720.2 Torr

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tributyl-amine; trimethylsilyl bromide; tetrabutylammonium tetrafluoroborate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0367602

Reference yield:

2,5-bis((tert-butyldimethylsilyl)oxy)furan + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 2,5-dihydroxy-4-methylbenzoic acid methyl ester (3899-19-2) + methyl 2,5-dihydroxy-3-methylbenzoate (160774-33-4)

Guidance literature:

2,5-bis((tert-butyldimethylsilyl)oxy)furan; acrylic acid methyl ester; In neat (no solvent); at 23 ℃; Schlenk technique; Inert atmosphere;

With methanol; at 65 ℃; Overall yield = 91 percent; Overall yield = 0.406 g; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.0c06306

upstream raw materials:

methanol

4-methyl-2,5-dihydroxybenzoic acid

carbon monoxide

2-bromo-5-methylbenzene-1,4-diol

Downstream raw materials:

(E)-3-(2,5-Bis-benzyloxy-4-methyl-phenyl)-acrylic acid ethyl ester

(E)-3-(2,5-Bis-benzyloxy-4-methyl-phenyl)-acrylonitrile

2,5-Bis-benzyloxy-4-methyl-benzonitrile

2,5-Bis-benzyloxy-4,N,N-trimethyl-benzamide

Refernces

• 1、 Zheng, Haifeng,Xu, Chaoran,Wang, Yan,Kang, Tengfei,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming. "Catalytic asymmetric [2+2] cycloaddition between quinones and fulvenes and a subsequent stereoselective isomerization to 2,3-dihydrobenzofurans". supporting information. p. 6585 - 6588. Retrieved 2017/07/10.
• 2、 -. "Utilization of derivatives of 2,5-dihydroxyphenyl-carboxylic acids, their homologs, and their salts in preparation of a cosmetic or dermatological composition with a depigmenting action". . . Retrieved 2008/06/13.