1-Methylcyclohexanecarboxylic acid → Methyl 1-methylcyclohexanecarboxylate

HRID 1993671Notes

Reaction equation

HRID 1993671 reaction equation
[CH3:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:11][Si](C=[N+]=[N-])(C)C>CO.CCOCC>[CH3:1][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 707441-Methylcyclohexanecarboxylic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 524785Methyl 1-methylcyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Treat a solution of 1-methylcyclohexane carboxylic acid (7.11 g, 50.0 mmol) in MeOH (10 mL) and Et2O (40 mL) dropwise with trimethylsilyldiazomethane (2.0 M/hexanes; 26 mL, 52 mmol). Stir the reaction mixture at room temperature overnight, then concentrate under reduced pressure to yield the title compound as a clear, pale yellow oil (7.811 g, 50 mmol; 100%). MS(ES): m/z=156 [M+H].

Workup

  1. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-a63ff77dc609498ba16d42897f5b6bfb
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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