Water → Dibenzyl ether

HRID 2405

Reaction equation

HRID 2405 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:9]>>[CH2:1]([OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:9][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 7503Benzyl Chloride

Product 2

HCID 244Benzyl AlcoholHCID 7657Dibenzyl etherYield 5.4%

Procedure

126.5 g (1 mol) of benzyl chloride and 180 g (10 mol) of water were rapidly heated to reflux in a flask with baffles and propeller stirrer with vigorous stirring (250 rpm) under nitrogen. After 240 min reaction time, the mixture was rapidly cooled, the organic phase was separated off after addition of toluene, and analyzed by gas chromatography. It was found that 48 g of the benzyl chloride had been converted to give a yield of benzyl alcohol of 37 g and about 3.6 g dibenzyl ether, corresponding to a conversion of 38% and a yield of benzyl alcohol of 91%. The hydrochloric acid formed had a concentration of about 7.4%.

Workup

  1. temperatureto reflux in a flask with baffles and propeller stirrer
  2. customAfter 240 min reaction time
  3. temperaturethe mixture was rapidly cooled
  4. customthe organic phase was separated off
  5. additionafter addition of toluene

Sources & evidence

ORD record
ord-ef5596a4da4243beba3c5680c17f513e
Source dataset
uspto-grants-1998_03
Patent number
US05728897

Linked notes

Loading…