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

HRID 1973859Notes

Reaction equation

HRID 1973859 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.[N+]([O-])(O)=O>>[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 5

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 7501StyreneHCID 149062-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, 183 parts of o-chlorostyrene and 117 parts of o-chloroethylbenzene is added to a mixture of 722 parts of 93 per cent strength by weight phosphoric acid and 7.5 parts of 65 per cent strength by weight nitric acid at 35° to 40° C over 5 hours. The emulsion is stirred for a further 2 hours at 35° to 40° C and the organic phase is then separated off and washed with 200 parts of 3 per cent strength by weight sodium hydroxide solution. Fractional distillation at 10 mm Hg gives 26 parts of 1-methyl-3-phenylindan and 148.5 parts of 1-methyl-3-(o-chloro)-phenylindan (b.p. 165° to 168° C (10 mm), nD25 : 1.5890).

Workup

  1. customthe organic phase is then separated off
  2. washwashed with 200 parts of 3 per cent strength by weight sodium hydroxide solution
  3. distillationFractional distillation at 10 mm Hg

Sources & evidence

ORD record
ord-db132c4385ff44e9a86e3991d544504e
Source dataset
uspto-grants-1976_12
Patent number
US03998894

Reaction notes

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