86791-22-2

Basic information

• Product Name: 2,3,6-trichloro-5-hydroxy-4,4-dimethyl-2,5-cyclohexadienone
• Synonyms: 2,3,6-trichloro-5-hydroxy-4,4-dimethyl-2,5-cyclohexadienone
• CAS NO: 86791-22-2
• Molecular Weight: 241.501
• Mol File: 86791-22-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,3,6-trichloro-5-hydroxy-4,4-dimethyl-2,5-cyclohexadienone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,6-trichloro-5-hydroxy-4,4-dimethyl-2,5-cyclohexadienone(86791-22-2)
• EPA Substance Registry System: 2,3,6-trichloro-5-hydroxy-4,4-dimethyl-2,5-cyclohexadienone(86791-22-2)

Safety Data

• Hazardous Substances Data: 86791-22-2(Hazardous Substances Data)

Upstream product

• 85544-63-4 2,3,5,6-tetrachloro-4,4-dimethyl-2,5-cyclohexadienone 

Downstream Products

• 86791-24-4 2,4,5-Trichloro-3-methoxy-6,6-dimethyl-cyclohexa-2,4-dienone 
• 86791-23-3 2,3,6-Trichloro-5-methoxy-4,4-dimethyl-cyclohexa-2,5-dienone 

Relevant articles and documents

HIGH YIELD SYNTHESIS OF FILICINIC ACID, BASED ON THE POLYCHLORINATION OF 4,4-DIMETHYL-2-CYCLOHEXENONE PART II : CONVERSION OF 2,3,5,6-TETRACHLORO-4,4-DIMETHYL-2,5-CYCLOHEXADIENONE INTO FILICINIC ACID AND RELATED CYCLOHEXADIENONES

Filicinic acid (5) was prepared in 75-80percent overall yield from 4,4-dimethyl-2-cyclohexenone (1).The key intermediate, tetrachlorodienone 2, underwent facile substitution of both β-chlorine substituents by methoxide affording the bis enol ether 3 which was converted into dichlorofilicinic acid 4 in hot 85percent sulfuric acid.Monohydroxy derivatives were obtained by treatment of 2 or 3 with hydroxide.Palladium-catalysed low-pressure hydrogenation of 4 under appropiate conditions produced monochlorofilicinic acid, filicinic acid or 5-hydroxy-4,4-dimethyl-1,3-cyclohexanedione (8) with high selectivity.