Benzyl Alcohol → Benzyl 2-oxocyclopentane-1-carboxylate

HRID 1875297Notes

Reaction equation

HRID 1875297 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].C(O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO>CN(C1C=CN=CC=1)C.C1CCCCC1>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 887MethanolHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 9794427Benzyl 2-oxocyclopentane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8078CyclohexaneSolvent

Procedure

In a 4-liter flask fitted with a Dean-Stark apparatus and a condenser, methyl 2-oxo-cyclopentanecarboxylate (380 mL; 3 mol), benzyl alcohol (342 mL; 3.3 mol; 1.1 eq.) and DMAP (18.3 g; 0.15 mol; 0.05 eq.) are dissolved in 1800 mL of cyclohexane. The reaction mixture is stirred for 48 hours at reflux (temperature of the mixture: 90° C.) and the methanol formed is distilled off. After cooling, the reaction mixture is concentrated and taken up in 1500 mL of dichloromethane. The organic phase is washed with 1N hydrochloric acid, with water, and then with saturated sodium chloride solution. It is then dried, filtered and then evaporated.

Workup

  1. temperatureat reflux (temperature of the mixture
  2. distillationis distilled off
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated
  5. washThe organic phase is washed with 1N hydrochloric acid, with water
  6. customIt is then dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-b3293e6fabe04d22bfe018ca0eb910d8
Source dataset
uspto-grants-2012_11
Patent number
US08309341B2

Reaction notes

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