Diazomethane → Cyclohexaneacetic acid, methyl ester

HRID 867780Notes

Reaction equation

HRID 867780 reaction equation
[CH:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH2:13])=[N-]>CCOCC>[CH:1]1([CH2:7][C:8]([O:10][CH3:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 21363Cyclohexaneacetic acid

Product 1

HCID 139743Cyclohexaneacetic acid, methyl esterYield 72.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ice-cooled and stirred solution of cyclohexylacetic acid (9.34 g, 0.066 mol) in 30 ml of ether was slowly added an excess solution of diazomethane in ether. After concentration of ether, the residue was distilled under reduced pressure to give a colorless transparent liquid of methyl cyclohexylacetate (7.45 g, 0.048 mol, yield 72.4%, b.p. 86°-88° C./12 mmHg), which was assigned the structure by the following data:

Workup

  1. distillationAfter concentration of ether, the residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-2562b137b85d48f0b94df6a1ac17178f
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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