Benzyl Alcohol → Benzyl 2-oxocyclopentane-1-carboxylate

HRID 331092Notes

Reaction equation

[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(O)[C:13]1[CH:18]=[CH:17]C=[CH:15][CH:14]=1>>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][C:11]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)=[O:8]

Participants

Reactant 2

HCID 244Benzyl Alcohol

HCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 9794427Benzyl 2-oxocyclopentane-1-carboxylateYield 93.1%

Conditions

Temperature: 175 °C

Procedure

To ethyl 2-oxocyclopentanecarboxylate (4 g, 25.6 mmol) was added benzyl alcohol (3.6 g, 33.3 mmol) and the resulting mixture was heated to 175° C. for 1 hour. The reaction mixture was concentrated under reduced pressure using a high vacuum pump to yield benzyl 2-oxocyclopentanecarboxylate (5.2 g, 23.84 mmol, 93% yield) as an oil. This compound was used for the next step without further purification.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-d7ac1bba13244c19ad37599836746015
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877749B2

Reaction notes

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