1,2,4,5-Tetrachlorobenzene → 2,3,4-Trichlorophenol

Reaction equation

ClC(Cl)(Cl)[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ClC1C=C(Cl)C(Cl)=CC=1Cl.[Cl-:22].[Cl-:23].[Cl-:24].[Al+3]>C1(C)C(C)=CC=CC=1>[Cl:22][C:7]1[CH:8]=[CH:9][C:4]([OH:3])=[C:5]([Cl:23])[C:6]=1[Cl:24]

Participants

Procedure

A mixture of trichloroanisole (0.1 g mol; 21.15 g) and 1,2,4,5-tetrachlorobenzene (10 g) in xylene (80 ml) was heated at 80° C. with aluminium trichloride (0.05 mole; 6.65 g) for five hours. Trichlorophenol was isolated in 97% yield (based on trichloroanisole) as described in Example I below. Unchanged tetrachlorobenzene, together with xylene self condensation product (total 13.25 g) was isolated from the neutral product fraction after solvent removal.