Cyclohexanecarboxylic acid → Methyl cyclohexanecarboxylate

HRID 867776Notes

Reaction equation

HRID 867776 reaction equation
[CH:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH2:12])=[N-]>CCOCC>[CH:1]1([C:7]([O:9][CH3:12])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7413Cyclohexanecarboxylic acidHCID 9550Diazomethane

Product 1

HCID 20748Methyl cyclohexanecarboxylateYield 67.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ice-cooled and stirred solution of cyclohexanecarboxylic acid (7.4 g, 0.058 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 cyclohexanecarboxylate (5.6 g, 0.039 mol, yield 67.2%, b.p. 73°-74° C./16 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-58f637fa3e114a79a9978acf4ce2f2d5
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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