Diazomethane → Methyl cyclohexanepropionate

HRID 867782Notes

Reaction equation

HRID 867782 reaction equation
[CH:1]1([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH2:14])=[N-]>CCOCC>[CH:1]1([CH2:7][CH2:8][C:9]([O:11][CH3:14])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 69702Cyclohexanepropanoic acid

Product 1

HCID 88651Methyl cyclohexanepropionateYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ice-cooled and stirred solution of 3-cyclohexylpropionic acid (5.0 g, 32.1 mmol) in 30 ml of ether was added an excess solution of diazomethane in ether. After concentration, the residue was distilled under reduced pressure to give a colorless transparent liquid of methyl 3-cyclohexylpropionate (4.8 g, 28.2 mmol, yield 88%, b.p. 95°-99° C./8 mmHg), which was assigned the structure by the following data:

Workup

  1. concentrationAfter concentration
  2. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-e88adf6fc2b7413cb78e39a74f2cdaf3
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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