P-Cresol → 2-Chloro-4-methylphenol

HRID 1457425Notes

Reaction equation

HRID 1457425 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Al+3].[Cl-:10].[Cl-].[Cl-].C1(SC2C=CC=CC=2)C=CC=CC=1.ClCl>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:10][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

6

Reactant 4

HCID 2879P-CresolHCID 8766Diphenyl sulfideHCID 24526ChlorineHCID 6451240Aluminum(III) Chloride

Product 2

HCID 2879P-CresolYield 0.03%HCID 148512-Chloro-4-methylphenolYield 93.2%

Procedure

100 parts by weight of 4-methylphenol were melted at ~35° C. and stirred. To this were added 1.5 parts by weight of AlCl3 and 0.95 part by weight of diphenyl sulphide. 74.6 parts by weight of gaseous chlorine were introduced uniformly in the course of 6 h, initially at 30°-31° C., later at 22°-25° C. After a short further stirring phase at approximately 25° C., 146.2 parts by weight of crude product were obtained of the GC composition 0.03% of 4-methylphenol and 93.20% of 2-chloro-4-methylphenol. Work-up by distillation produced 127.8 parts by weight of pure distillate having a GC content of 0.03% of 4-methylphenol, 99.92% of 2-chloro-4-methylphenol and 0.05% of unknown.

Sources & evidence

ORD record
ord-b2efd69a97344b859e7228f8cb09bffa
Source dataset
uspto-grants-1998_12
Patent number
US05847236

Reaction notes

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