Allyl bromide → 2-(o-Tolylthio)-6-allylphenol

HRID 1164104Notes

Reaction equation

HRID 1164104 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].[CH2:16](Br)[CH:17]=[CH2:18].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:18][CH:17]=[CH2:16])[C:9]=1[OH:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 154566642-(o-Tolylthio)phenol

Product 1

HCID 130666692-(o-Tolylthio)-6-allylphenolYield 62.7%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 2-(o-tolylthio)phenol (32.7 g), allyl bromide (27.5 g) and dried potassium carbonate (42 g) in methyl isobutyl ketone (400 ml) was refluxed under heating for 4 hours. The reaction mixture was treated in the same manner as Example 21-(1) to give oily 2-(o-tolylthio)-6-allylphenol (24.3 g), bp. 150°-162° C./0.7-0.8 mmHg.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 4 hours

Sources & evidence

ORD record
ord-3e4edbe4c21f403b855ec63df725a467
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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