Methanol → Methyl o-toluate

HRID 2427578Notes

Reaction equation

HRID 2427578 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11](Cl)(=O)C(Cl)=O.CO.C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:11][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 887MethanolHCID 83732-Methylbenzoic acidHCID 8471TriethylamineHCID 65578Oxalyl chloride

Product 1

HCID 33094Methyl o-toluate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-benzoic acid (1.36 g, 10 mmol) in dichloromethane (10 mL) was treated with oxalyl chloride (6 mL, 12 mmol) and dimethylformamide (several drops) followed by treatment with methanol (10 mL) and triethylamine (2.78 mL, 20 mmol). Workup afforded 2-methyl-benzoic acid methyl ester. The material was used without further purification.

Sources & evidence

ORD record
ord-e42b30cf6615460ca2865f359bbd93b5
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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