Phenol → 2-(Ethylthio)phenol

HRID 745691Notes

Reaction equation

HRID 745691 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([S:10]SCC)[CH3:9]>[O-]C1C=CC=CC=1.[Zr+4].[O-]C1C=CC=CC=1.[O-]C1C=CC=CC=1.[O-]C1C=CC=CC=1>[CH2:8]([S:10][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])[CH3:9]

Participants

4

Reactant 2

HCID 996PhenolHCID 8077Diethyl disulfide

Product 1

HCID 1224072-(Ethylthio)phenolYield 38%

Reagents, catalysts & solvents 1

HCID 13847644Zirconium(2+);tetraphenoxideCatalyst

Conditions

Temperature
195 °C

Procedure

Zirconium phenoxide (4.0 g, 0.0086 moles) was added to phenol (8.9 g, 0.095 moles) and ethyl disulfide (10.5 g, 0.086 moles). The mixture was heated under nitrogen for 6.5 hours during which the temperature slowly increased to 195° C. Ethyl mercaptan was removed continuously by distillation. The mixture was distilled at 0.4 mm mercury to a maximum head temperature of 102° C. yielding 12.2 g of distillate. Gas chromatographic (GC) analysis indicated the distillate contained 5.0 g of ortho-(ethylthio)phenol (38% yield).

Workup

  1. temperatureThe mixture was heated under nitrogen for 6.5 hours during which the temperature
  2. customEthyl mercaptan was removed continuously by distillation
  3. distillationThe mixture was distilled at 0.4 mm mercury to a maximum head temperature of 102° C.
  4. customyielding 12.2 g of distillate

Sources & evidence

ORD record
ord-d5c6c32db05f45e4a3c4fbb957a38a0f
Source dataset
uspto-grants-1986_07
Patent number
US04599451

Reaction notes

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