Phosphoric Acid → 1-Methyl-3-phenyl-2,3-dihydro-1H-indene
Reaction equation
C1C2NC3C(=CC=CC=3)SC=2C=CC=1.P(=O)(O)(O)O.[CH2:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.ClC1C=CC=CC=1C=C.Cl[CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH3:38][CH:39]1[C:40]2[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20]1Participants
Conditions
- Temperature
- 38 °C
Procedure
1 part of phenothiazine is added to 375 parts by volume of phosphoric acid (95% strength by weight) at 25° C, in a stirred vessel. The mixture is irradiated for 10 minutes with a mercury vapor lamp (15 watt hours per kilogram of styrene II and III) whilst passing 2,000 parts of air through it. A mixture of 52 parts of styrene, 78 parts of o-chlorostyrene and 42 parts of o-chloroethylbenzene is then added to the irradiated solution over 3 hours at a temperature of 38° C. After completion of the addition, the mixture is stirred for a further hour at 38° C. The organic phase is separated off, washed with 200 parts of 5 per cent strength by weight sodium hydroxide solution and fractionated. 13.8 parts of 1-methyl-3-phenylindan (b.p. 145° to 146° C (10 mm)), 85 parts of 1-methyl-3-(o-chloro)-phenylindan (b.p. 165° to 168° C (10 mm), nD25 : 1.5890) and 5 parts of 1-methyl-3-(o-chloro)-phenyl-7-chloroindan (b.p. 195° to 200° C (10 mm)) are isolated.
Workup
- additionis then added to the irradiated solution over 3 hours at a temperature of 38° C
- additionAfter completion of the addition
- customThe organic phase is separated off
- washwashed with 200 parts of 5 per cent strength by weight sodium hydroxide solution
Sources & evidence
- ORD record
- ord-2b46a3e186b840518ad23707a240dc36
- Source dataset
- uspto-grants-1976_12
- Patent number
- US03998894
Reaction notes
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