P-Xylene → Chloro-p-xylene

HRID 851800Notes

Reaction equation

HRID 851800 reaction equation
CS(Cl)(=O)=O.[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=1.[Al+3].[Cl-:15].[Cl-].[Cl-]>>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[Cl:15]

Participants

4

Reactant 3

HCID 7809P-XyleneHCID 31297Methanesulfonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 32883Chloro-p-xyleneYield 70%

Conditions

Temperature
25 °C

Procedure

A mixture of 2.3 g (0.02 mole) of methanesulfonyl chloride, 20 ml (0.16 mole) of p-xylene, and 3.1 g (0.023 mole) of AlCl3 was stirred for one hour at 25° C. The product was worked up as described above in Example 1. 2,5-dimethylchlorobenzene was obtained in a 70% yield. NMR and VPC analysis of the crude product showed the presence of less than 1% of 2,5-dimethylphenyl methyl sulfone.

Sources & evidence

ORD record
ord-4d7ebc21ea96432382d3c5a66beefe29
Source dataset
uspto-grants-1983_05
Patent number
US04386221

Reaction notes

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