Salicyl Alcohol → 2-[(Ethylsulfanyl)methyl]phenol

HRID 2198592

Reaction equation

HRID 2198592 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[CH2:10]([SH:12])[CH3:11]>ClC1C=CC=CC=1Cl>[CH2:10]([S:12][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])[CH3:11]

Participants

4

Reactant 2

HCID 5146Salicyl AlcoholHCID 6343Ethanethiol

Product 1

HCID 5221672-[(Ethylsulfanyl)methyl]phenolYield 87%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 49.6 g (0.4 mol) of 2-hydroxymethyl-phenol, 24.8 g (0.4 mol) of ethylmercaptan and 200 ml of o-dichlorobenzene was heated in a flask equipped with a stirrer and a reflux condenser, under normal pressure, and starting from room temperature, in such a way that there was always a moderate reflux and that the final temperature in the flask did not exceed about 125° C. In total, the mixture was heated under reflux for about 20 hours. Thereafter, working up by distillation gave 2-ethylthiomethyl-phenol in a yield of 87% of theory. The o-dichlorobenzene distilled off could be re-used in a subsequent batch.

Workup

  1. temperaturewas heated in a flask
  2. customequipped with a stirrer and a reflux condenser, under normal pressure
  3. customstarting from room temperature
  4. temperaturea moderate reflux
  5. customdid not exceed about 125° C
  6. temperatureIn total, the mixture was heated
  7. temperatureunder reflux for about 20 hours
  8. distillationThereafter, working up by distillation

Sources & evidence

ORD record
ord-85871db35598409f84503505060a132e
Source dataset
uspto-grants-1982_11
Patent number
US04358616

Linked notes

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