Methanol → Methyl 2-chloro-6-methylbenzoate

HRID 2427579Notes

Reaction equation

HRID 2427579 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(=O)C(Cl)=O.CO.C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:12][O:5][C:4](=[O:6])[C:3]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 888702-Chloro-6-methylbenzoic acid

Product 1

HCID 22935202Methyl 2-chloro-6-methylbenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-chloro-6-methyl-benzoic acid (1.70 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-chloro-6-methyl-benzoic acid methyl ester. The material was used without further purification.

Sources & evidence

ORD record
ord-82c26bd18e6249b995a2ff8741fe69c1
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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