Potassium Hydroxide → 2-(o-Tolylthio)-6-(1-propenyl)phenol

HRID 1164105Notes

Reaction equation

HRID 1164105 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]=[CH2:16])[C:9]=1[OH:17].[OH-].[K+]>CO>[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[CH:15][CH3:16])[C:9]=1[OH:17]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 130666692-(o-Tolylthio)-6-allylphenol

Product 1

HCID 544721892-(o-Tolylthio)-6-(1-propenyl)phenolYield 101.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(o-tolylthio)-6-allylphenol (24 g) and potassium hydroxide (32 g) in methanol (100 ml) was stirred at 110° C. Methanol was distilled off from the mixture under ordinal pressure, and the mixture was stirred at 100° C. for an hour. The reaction mixture was cooled, acidified with conc. hydrochloric acid and extracted with diethyl ether. The extract was washed with water, dried and evaporated under reduced pressure to give oily 2-(o-tolylthio)-6-(1-propenyl)phenol (24.3 g).

Workup

  1. distillationMethanol was distilled off from the mixture under ordinal pressure
  2. stirringthe mixture was stirred at 100° C. for an hour
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with diethyl ether
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b8409a1ca364426c9b8b0c2eb35354fc
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

Loading…