Thionyl Chloride → 1-(Chloromethyl)-4-phenoxybenzene

HRID 1276937Notes

Reaction equation

HRID 1276937 reaction equation
S(Cl)([Cl:3])=O.[O:5]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16]O)=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[O:5]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][Cl:3])=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 826195(4-Phenoxyphenyl)methanol

Product 1

HCID 5209941-(Chloromethyl)-4-phenoxybenzeneYield 97.2%

Conditions

Temperature
80 °C

Procedure

Thionyl chloride (13.34 g) was added to 4.06 g of 4-phenoxybenzyl alcohol, and the mixture was stirred at 80° C. for 3.5 hours. After the completion of the concentration, the reaction mixture was extracted with ethyl acetate and with water. The organic layer was concentrated to give 4.31 g of 4-phenoxybenzyl chloride.

Workup

  1. concentrationAfter the completion of the concentration
  2. extractionthe reaction mixture was extracted with ethyl acetate and with water
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-8f000ac0c48e4b09813cc2ececd1345e
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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