Diazomethane → Methyl cyclopentanecarboxylate

HRID 867774Notes

Reaction equation

HRID 867774 reaction equation
[CH:1]1([C:6]([OH:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH2:11])=[N-]>CCOCC>[CH:1]1([C:6]([O:8][CH3:11])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 18840Cyclopentanecarboxylic acid

Product 1

HCID 78365Methyl cyclopentanecarboxylateYield 85.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ice-cooled and stirred solution of cyclopentanecarboxylic acid (8.0 g, 0.070 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 oil of methyl cyclopentanecarboxylate (7.65 g, 0.053 mol, yield 85.2%, b.p. 82°-83° C./62 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-eb3aa9c8590c495cb401d78bfdf986c1
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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