Benzyl Alcohol → Benzyl phenylacetate

HRID 1706274Notes

Reaction equation

HRID 1706274 reaction equation
[I-].BrC1C=CC=C[N+]=1C.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18]1([CH2:24][C:25](O)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CCCC)CCCC)CCC>C(Cl)Cl>[C:18]1([CH2:24][C:25]([O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 999Phenylacetic AcidHCID 7622TributylamineHCID 122339072-Bromo-1-methylpyridinium iodide

Product 1

HCID 60999Benzyl phenylacetateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspended CH2Cl2 (2 ml) solution of 2-bromo-1-methylpyridinium iodide (720 mg, 2.4 mmol) was added a mixture of benzyl alcohol (216 mg, 2.0 mmol), phenylacetic acid (272 mg, 2.0 mmol) and tri-n-butylamine (888 mg, 4.8 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 97% 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-db3c05da40fb4e899b9926f886f085ae
Source dataset
uspto-grants-1980_06
Patent number
US04206310

Reaction notes

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