O-Cresol → 4-Chloro-2-methylphenol

HRID 67196

Reaction equation

HRID 67196 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]1([CH3:13])[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][CH:7]=1>>[Cl:4][C:8]1[CH:7]=[C:6]([CH3:13])[C:11]([OH:12])=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 335O-Cresol2×HCID 24648Sulfuryl chloride2×

Product 1

HCID 148554-Chloro-2-methylphenolYield 84%

Procedure

The chlorination of aromatic compounds with sulfuryl chloride is generally known. For example, DuBois in Z. F. Chem. 705 (1866) reported that treatment of molten phenol with an equal molar amount of sulfuryl chloride yields only p-chlorophenol. Sulfuryl chloride was first reported as a chlorinating agent for o-cresol by Sah and Anderson in J. Am. Chem. Soc. 63, 3164 (1941). Their data showed that o-cresol reacted with sulfuryl chloride to yield 84% of the 4-chloro-o-cresol.

Sources & evidence

ORD record
ord-6de4de661824448bb1353af245631ff8
Source dataset
uspto-grants-1982_08
Patent number
US04345097

Linked notes

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