Benzyl Alcohol → Benzyl phenylacetate

HRID 1833792Notes

Reaction equation

HRID 1833792 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). ##STR263##

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-7d4a15ff76264720abce441153d88949
Source dataset
uspto-grants-1978_01
Patent number
US04066831

Reaction notes

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