Benzyl Alcohol → Benzyl phenylacetate

HRID 1706283Notes

Reaction equation

HRID 1706283 reaction equation
[I-].C([N+]1C2C(=CC=CC=2)C=CC=1I)C.[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:23]1([CH2:29][C:30](O)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CCCC)CCCC)CCC>C(Cl)Cl>[C:23]1([CH2:29][C:30]([O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 999Phenylacetic AcidHCID 7622TributylamineHCID 78526Quinolinium, 1-ethyl-2-iodo-, iodide (1:1)

Product 1

HCID 60999Benzyl phenylacetateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspended CH2Cl2 (2 ml) solution of 1-ethyl-2-iodoquinolinium iodide (493 mg, 1.2 mmol) was added a mixture of benzyl alcohol (108 mg, 1.0 mmol), phenylacetic acid (136 mg, 1.0 mmol) and tri-n-butylamine (444 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-0deee1ad33a44f76b7a6c5deddb69a74
Source dataset
uspto-grants-1980_06
Patent number
US04206310

Reaction notes

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