Phosphoric Acid → 1-Methyl-3-phenylindane

Participants

Reaction Steps

A mixture of 115 parts of o-chlorostyrene and 35 parts of o-chloroethylbenzene is added to a mixture of 652 parts of 78 per cent strength by weight phosphoric acid and 20 parts of sulfuric acid monohydrate at 30° to 35° C, whilst stirring vigorously. A mixture of 90 parts of styrene, 115 parts of o-chlorostyrene and 35 parts of o-chloroethylbenzene is then added at 30° to 35° C over 5 hours. After completion of the addition, the mixture is stirred for a further 2 hours and the organic phase is separated off and washed with 200 parts of 3 per cent strength by weight sodium hydroxide solution. Fractional distillation at 10 mm Hg gives 25 parts of 1-methyl-3-phenylindan, 30 parts of 1-methyl-3-(o-chloro)-phenylindan (b.p. 165° to 168° C (10 mm), nD25 : 1.5890) and 28 parts of 1-methyl-3-(o-chloro)-phenyl-7-chloroindan (b.p. 195° to 200° C (10 mm)).

Provenance & Evidence