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

HRID 2198589

Reaction equation

HRID 2198589 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]>O>[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 6343Ethanethiol2×

Product 1

HCID 5221672-[(Ethylsulfanyl)methyl]phenolYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 99.2 g (0.8 mol) of 2-hydroxymethyl-phenol and 124 g (2 mol) of ethylmercaptan was heated for 5 hours to 170° C. in a VA autoclave, whilst stirring. After cooling to room temperature, the unconverted ethylmercaptan and the water of reaction were distilled off under normal pressure, and subsequently the 2-ethylthiomethyl-phenol was distilled off under 1.5 mm Hg. 128 g of 2-ethylthiomethyl-phenol (ca. 95% of theory) were obtained.

Workup

  1. temperaturewas heated for 5 hours to 170° C. in a VA autoclave
  2. distillationwere distilled off under normal pressure
  3. distillationsubsequently the 2-ethylthiomethyl-phenol was distilled off under 1.5 mm Hg

Sources & evidence

ORD record
ord-032b17f7153c419392411b40e010db18
Source dataset
uspto-grants-1982_11
Patent number
US04358616

Linked notes

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