Ethanol → Ethyl phenylacetate

HRID 1706279Notes

Reaction equation

HRID 1706279 reaction equation
F[B-](F)(F)F.Cl[C:7]1[CH:12]=CC=C(Cl)[N+]=1CC.C(O)C.[C:19]1([CH2:25][C:26]([OH:28])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CCCC)CCCC)CCC>C(Cl)Cl>[C:19]1([CH2:25][C:26]([O:28][CH2:7][CH3:12])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 999Phenylacetic AcidHCID 7622TributylamineHCID 20337649HCID 20337649, compound

Product 1

HCID 7590Ethyl phenylacetateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a CH2Cl2 (2 ml) solution of 2,6-dichloro-1-ethylpyridinium tetrafluoroborate (630 mg, 2.4 mmol) was added a mixture of ethyl alcohol (92 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 ethyl phenylacetate was isolated in 90% 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-1c779fcf800e43d7ac8f300a7242b442
Source dataset
uspto-grants-1980_06
Patent number
US04206310

Reaction notes

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