Benzyl Bromide → Benzyl 4-oxocyclohexane-1-carboxylate

HRID 2375453Notes

Reaction equation

HRID 2375453 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[C:18]1([CH2:17][O:9][C:8]([CH:5]2[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]2)=[O:10])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1927304-Oxocyclohexanecarboxylic acid

Product 1

HCID 15395052Benzyl 4-oxocyclohexane-1-carboxylateYield 84.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To an acetone solution containing 12.0 g (84.4 mmol) of 4-ketocyclohexane carboxylic acid and 4.7 g (33.8 mmol) of potassium carbonate, 17.3 g (101.3 mmol) of benzyl bromide was added at room temperature. Next, this was agitated at 60° C. for 3 hours. After the reaction ended, crude product was obtained, and after potassium carbonate was removed by filtration and acetone was evaporated, the crude product was purified by silica gel column chromatography, and 16.5 g of 4-ketocyclohexane carboxylic acid phenylmethyl ester was obtained.

Workup

  1. additionwas added at room temperature
  2. customcrude product was obtained
  3. customafter potassium carbonate was removed by filtration and acetone
  4. customwas evaporated
  5. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6dbcbeeb20a34db48619d7664760565e
Source dataset
uspto-grants-2008_12
Patent number
US07465779B2

Reaction notes

Loading…