O-Cresol → Benzene, 1-methyl-2-(phenylmethoxy)-

HRID 1380553Notes

Reaction equation

HRID 1380553 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+]>O.C(O)C>[CH2:9]([O:7][C:6]1[C:1]([CH3:8])=[CH:2][CH:3]=[CH:4][CH:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 335O-CresolHCID 7503Benzyl ChlorideHCID 14797Potassium Hydroxide

Product 1

HCID 96385Benzene, 1-methyl-2-(phenylmethoxy)-Yield 76.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

o-Cresol (50 g), 70 g of benzyl chloride and 38.5 g of potassium hydroxide were boiled in a mixture of 100 ml of water and 500 ml of ethanol for 4 hours. The solvent was then distilled off and the residue was shaken with 500 ml each of water and diethyl ether. The diethyl ether layer was washed with 10% sodium hydroxide and water in that order, and distilled under reduced pressure to give 70 g of an O-benzylcresol fraction boiling at 130°-133° C./5 mmHg.

Workup

  1. distillationThe solvent was then distilled off
  2. washThe diethyl ether layer was washed with 10% sodium hydroxide and water in that order
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c8b91e274db4423d912af6e98ba59db8
Source dataset
uspto-grants-1986_04
Patent number
US04582847

Reaction notes

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