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

HRID 1973854Notes

Reaction equation

HRID 1973854 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ClC1C=CC=CC=1C=C.Cl[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.P(=O)(O)(O)O>ClC1C=CC=CC=1Cl>[CH3:19][CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:1]1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 7501StyreneHCID 149062-ChlorostyreneHCID 2314961-Chloro-2-phenylethane

Product 1

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

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 90 parts of styrene, 156 parts of o-chlorostyrene and 114 parts of o-chloroethylbenzene is added to an emulsion of 680 parts of 90 per cent strength by weight phosphoric acid and 150 parts of o-dichlorobenzene at 35° to 40° C over 5 hours, whilst stirring vigorously. The mixture is stirred for a further 2 hours at 35° to 40° C 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 34 parts of 1-methyl-3-phenylindan, 71 parts of 1-methyl-3-(o-chloro)-phenylindan (b.p. 165° to 168° C (10 mm), nD25 : 1.5890) and 23 parts of 1-methyl-3-(o-chloro)-phenyl-7-chloroindan (b.p. 195° to 200° C (10 mm)).

Workup

  1. stirringThe mixture is stirred for a further 2 hours at 35° to 40° C
  2. customthe organic phase is separated off
  3. washwashed with 200 parts of 3 per cent strength by weight sodium hydroxide solution
  4. distillationFractional distillation at 10 mm Hg

Sources & evidence

ORD record
ord-d444e34781114f6382ab574b5429df45
Source dataset
uspto-grants-1976_12
Patent number
US03998894

Reaction notes

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