Benzyl Alcohol → Benzyl phenylacetate

HRID 462306

Reaction equation

HRID 462306 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). ##STR230##

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-b6015e5e9c4f4828894d6a1ff668db79
Source dataset
uspto-grants-1977_12
Patent number
US04065623

Linked notes

Loading…