Benzyl Alcohol → Benzyl phenylacetate

HRID 427001

Reaction equation

HRID 427001 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[C:1]1([CH2:7][C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 999Phenylacetic AcidHCID 1140TolueneHCID 6101p-Toluenesulfonic acid

Product 1

HCID 60999Benzyl phenylacetateYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of phenyl acetic acid (27.2 g.), benzyl alcohol (21.6 g.) and p-toluenesulfonic acid (380 mg.) in 100 ml. of toluene was heated under reflux under a Dean-Stark trap until the theoretical (3.6 ml.) quantity of water had been collected. On cooling, the solution was washed with dilute NaHCO3 and saturated NaCl and solvent was removed in vacuo. The resulting oil was distilled at 125°-129° (0.4 torr)1 to give pure benzyl phenylacetate, 37.7 g. (83% yield). ##STR229##

Workup

  1. customhad been collected
  2. temperatureOn cooling
  3. washthe solution was washed with dilute NaHCO3 and saturated NaCl and solvent
  4. customwas removed in vacuo
  5. distillationThe resulting oil was distilled at 125°-129° (0.4 torr)1

Sources & evidence

ORD record
ord-8d53dd230d5a4681bddf3c81b088649d
Source dataset
uspto-grants-1979_10
Patent number
US04172199

Linked notes

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