4-Hydroxybenzyl Alcohol → Phenol, 4-[(ethylthio)methyl]-

HRID 2198593Notes

Reaction equation

HRID 2198593 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH2:10]([SH:12])[CH3:11].C1(O)C=CC=CC=1>>[CH2:10]([S:12][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)[CH3:11]

Participants

4

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 996PhenolHCID 6343Ethanethiol

Product 1

HCID 11469305Phenol, 4-[(ethylthio)methyl]-Yield 65%

Conditions

Temperature
85 °C

Procedure

A mixture of 62 g (0.5 mol) of 4-hydroxymethyl-phenol, 37 g (0.6 mol) of ethylmercaptan and 230 g of phenol was first heated, in a flask equipped with stirrer and reflux condenser, under normal pressure to about 85° C. in the course of about 15 minutes, and was then heated further in such a way that there was always a moderate reflux and that ultimately a final temperature of about 130° C. in the flask was reached. After a reaction time of 18 hours at 85°-130° C., the mixture was cooled and worked up by distillation. 4-Ethylthiomethyl-phenol was obtained in a yield of 65% of theory.

Workup

  1. temperaturewas first heated, in a flask
  2. customequipped with stirrer
  3. temperaturereflux condenser
  4. temperaturea moderate reflux
  5. customtemperature of about 130° C.
  6. temperatureAfter a reaction time of 18 hours at 85°-130° C., the mixture was cooled
  7. distillationworked up by distillation

Sources & evidence

ORD record
ord-9fd21d3d36b04fc0b927571eaf3ad146
Source dataset
uspto-grants-1982_11
Patent number
US04358616

Reaction notes

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