Phosphoric Acid → 1-Methyl-3-phenyl-2,3-dihydro-1H-indene

HRID 1973857Notes

Reaction equation

HRID 1973857 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[CH2:15])=[CH:12][CH:11]=1.ClCCC1C=CC=CC=1.P(=O)(O)(O)O>>[CH3:15][CH:14]1[C:13]2[C:12](=[CH:11][CH:10]=[CH:17][CH:16]=2)[CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:1]1

Participants

5

Reactant 4

HCID 1004Phosphoric AcidHCID 7501StyreneHCID 140854-ChlorostyreneHCID 2314961-Chloro-2-phenylethane

Product 1

HCID 229241-Methyl-3-phenyl-2,3-dihydro-1H-indene

Procedure

A mixture of 90 parts of styrene, 234 parts of p-chlorostyrene and 66 parts of p-chloroethylbenzene is added to 722 parts of 93 per cent strength by weight phosphoric acid at 35° to 40° C over 5 hours. After a further 2 hours at 35° to 40° C the organic phase is separated off and washed with 200 parts of 3 per cent strength by weight sodium hydroxide solution. Fractional distillation gives 16 parts of 1-methyl-3-phenylindan, 78 parts of 1-methyl-3-(p-chloro)-phenylindan (b.p. 166° to 170° C (10 mm), nD25 : 1.5869) and 13 parts of 1-methyl-3-(p-chloro)-phenyl-5-chloroindan (b.p. 197° to 204° C (10 mm)).

Workup

  1. customAfter a further 2 hours at 35° to 40° C the organic phase is separated off
  2. washwashed with 200 parts of 3 per cent strength by weight sodium hydroxide solution
  3. distillationFractional distillation

Sources & evidence

ORD record
ord-8072be3216724c839305b18334384905
Source dataset
uspto-grants-1976_12
Patent number
US03998894

Reaction notes

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