Allyl bromide → 2-(2-Chlorophenylthio)-6-allylphenol

HRID 1164075Notes

Reaction equation

HRID 1164075 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15].[CH2:16](Br)[CH:17]=[CH2:18].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:18][CH:17]=[CH2:16])[C:10]=1[OH:15]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 205134692-(2-Chlorophenylthio)phenol

Product 1

HCID 130666682-(2-Chlorophenylthio)-6-allylphenolYield 83.5%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 2-(2-chlorophenylthio)phenol (33 g), allyl bromide (25 g) and dried potassium carbonate (29 g) in methyl isobutyl ketone (200 ml) was refluxed under heating for 1.5 hours. After cooling to the ambient temperature, the reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The resultant oily residue was stirred at 230° C. for 3 hours and then distilled under reduced pressure to give oily 2-(2-chlorophenylthio)-6-allylphenol (32.2 g) bp 157°-162° C./0.7 mmHg.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 1.5 hours
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-e1215f4f06b9471583ca78ed7edf3cc8
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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