Phenol → 2-(Ethylthio)phenol

HRID 745694Notes

Reaction equation

HRID 745694 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]>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4].C1(C)C=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

5

Reactant 2

HCID 996PhenolHCID 8077Diethyl disulfide

Product 1

HCID 1224072-(Ethylthio)phenolYield 46.7%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 1140TolueneSolvent

Procedure

A similar run using phenol (142 g, 1.51 moles), toluene (150 ml), zirconium tetrachloride (6.0 g, 0.026 moles), and ethyl disulfide (62.0 g, 0.50 moles) gave ortho-(ethylthio)phenol (36.0 g, 46% yield).

Sources & evidence

ORD record
ord-e4887f21a3f74dd6bf3261b09ed5f067
Source dataset
uspto-grants-1986_07
Patent number
US04599451

Reaction notes

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