O-Cresol → 4-Chloro-2-methylphenol
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]=1Participants
3
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
Reaction notes
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