Benzyl Alcohol → Benzyl phenylacetate

HRID 1706275Notes

Reaction equation

HRID 1706275 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([CH2:15][C:16](O)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[C:9]1([CH2:15][C:16]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 999Phenylacetic AcidHCID 8471Triethylamine

Product 1

HCID 60999Benzyl phenylacetateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a CH2Cl2 (2ml) solution of 2-chloro-1-ethyl-4-methoxypryridinium tetrafluoroborate (296 mg, 1.2 mmol) was added a mixture of benzyl alcohol (108 mg, 1.0 mmol), phenylacetic acid (136 mg, 1.0 mmol) and triethylamine (243 mg, 2.4 mmol) in CH2Cl2 (2 ml), and the resulting mixture was refluxed for 3 hours. After evaporation of the solvent, the residue was separated by silica gel column chromatography, and benzyl phenylacetate was isolated in 95% yield.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours
  2. customAfter evaporation of the solvent
  3. customthe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-1c9afc29cfee4d45841730cd8fd8ba40
Source dataset
uspto-grants-1980_06
Patent number
US04206310

Reaction notes

Loading…