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

HRID 1973862Notes

Reaction equation

HRID 1973862 reaction equation
P(=O)(O)(O)O.[CH:6]1C2NC3C(=CC=CC=3)SC=2C=CC=1.[CH2:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH3:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1Cl)=[CH2:30].[Cl:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[CH:45]([CH3:47])[CH3:46]>>[CH3:28][CH:29]1[C:31]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:30]1.[CH3:26][CH:25]1[C:24]2[C:47](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:45]([CH3:6])([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[Cl:38])[CH2:46]1

Participants

7

Reactant 5

HCID 1004Phosphoric AcidHCID 7108PhenothiazineHCID 7501StyreneHCID 16377o-ChlorocumeneHCID 10968208HCID 10968208, compound

Product 2

HCID 229241-Methyl-3-phenyl-2,3-dihydro-1H-indeneHCID 21490570HCID 21490570, compound

Conditions

Temperature
40 °C

Procedure

A mixture of 375 parts of phosphoric acid (95% strength by weight) and 1 part of phenothiazine is irradiated for 10 minutes analogously to Example 11. A mixture of 52 parts of styrene, 76 parts of α-methyl-o-chlorostyrene and 94 parts of o-chloro-isopropylbenzene is added to the irradiated solution over 4 hours at 35° to 40° C. After completion of the addition, the mixture is stirred for a further hour at 40° C. The organic phase is separated off and washed with 150 parts of 5 per cent strength by weight sodium hydroxide solution, and fractional distillation gives 20 parts of 1-methyl-3-phenylindan and 68 parts of 1,3-dimethyl-3-(o-chlorophenyl)-indan (b.p. 147° to 152° C (0.4 mm)).

Workup

  1. customis irradiated for 10 minutes analogously to Example 11
  2. additionis added to the irradiated solution over 4 hours at 35° to 40° C
  3. additionAfter completion of the addition
  4. customThe organic phase is separated off
  5. washwashed with 150 parts of 5 per cent strength by weight sodium hydroxide solution, and fractional distillation

Sources & evidence

ORD record
ord-39fec260c9134dea8777484c293dc207
Source dataset
uspto-grants-1976_12
Patent number
US03998894

Reaction notes

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