Benzyl Alcohol → Benzyl 2-oxocyclopentane-1-carboxylate

HRID 2309554Notes

Reaction equation

HRID 2309554 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])=[O:4].C(O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:1]([O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 244Benzyl AlcoholHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 9794427Benzyl 2-oxocyclopentane-1-carboxylate

Conditions

Temperature
120 °C

Procedure

A mixture of 50 g. of methyl-2-oxocylopentanecarboxylate and 50 g. of redistilled benzyl alcohol was heated at 160° C. under a stream of nitrogen in a 500 ml. flask for 20 hours. Methanol distilled off as it was formed. The reaction mixture was subsequently cooled and the mixture distilled on the kugelrohr apparatus. The benzyl alcohol was removed by heating to 120° C. at 2 mm and the benzyl ester collected at 130° C. Yield was 45 g. (59%).

Workup

  1. additionA mixture of 50 g
  2. distillationMethanol distilled off as it
  3. customwas formed
  4. temperatureThe reaction mixture was subsequently cooled
  5. distillationthe mixture distilled on the kugelrohr apparatus
  6. customThe benzyl alcohol was removed
  7. customthe benzyl ester collected at 130° C

Sources & evidence

ORD record
ord-ff53ed52d4e043ff80b741b5cce882fc
Source dataset
uspto-grants-1987_09
Patent number
US04695647

Reaction notes

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