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

HRID 1973852Notes

Reaction equation

HRID 1973852 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH2:5].Cl[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P(=O)(O)(O)O.O.S(=O)(=O)(O)O.C=CC1C=CC=CC=1>>[CH3:11][CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:2]=2)[CH2:5]1

Participants

6

Reactant 5

HCID 1004Phosphoric AcidHCID 7501StyreneHCID 149062-Chlorostyrene2×HCID 2314961-Chloro-2-phenylethane2×HCID 21910475Sulfuric acid hydrate (1:1)

Product 1

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

Procedure

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)).

Workup

  1. additionis then added at 30° to 35° C over 5 hours
  2. additionAfter completion of the addition
  3. stirringthe mixture is stirred for a further 2 hours
  4. customthe organic phase is separated off
  5. washwashed with 200 parts of 3 per cent strength by weight sodium hydroxide solution
  6. distillationFractional distillation at 10 mm Hg

Sources & evidence

ORD record
ord-b188a2121a5648938a850edd9d1dba36
Source dataset
uspto-grants-1976_12
Patent number
US03998894

Reaction notes

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