Methanol → Methyl 4-hydroxy-2-methylbenzoate

HRID 1194562Notes

Reaction equation

HRID 1194562 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]O>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 684754-Hydroxy-o-toluic acid

Product 1

HCID 12351986Methyl 4-hydroxy-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

2-Methyl-4-hydroxybenzoic acid was heated in methanol under the influence of sulfuric acid catalyst to convert it into its methyl ester. One mole of the methyl 2-methyl-4-hydroxybenzoate thus obtained was reacted with two moles of hydrogen in the presence of palladium-carbon catalyst. This reaction was carried out in isopropyl alcohol at a temperature of 150°-170° C. and a hydrogen pressure of 20-40 kg/cm2. After the reaction mixture was filtered to recover the catalyst therefrom, the filtrate was distilled to obtain 3-methylcyclohexanone-4-carboxylic acid methyl ester as the distillate at 112°-120° C./5 mmHg.

Sources & evidence

ORD record
ord-e5ca94db05344a309dd17ebeb8ea3341
Source dataset
uspto-grants-1989_03
Patent number
US04814488

Reaction notes

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