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

HRID 1973861Notes

Reaction equation

HRID 1973861 reaction equation
P(=O)(O)(O)O.C1C2NC3C(=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.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[CH2:34])=[CH:31][CH:30]=1.Cl[CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH3:34][CH:33]1[C:32]2[C:31](=[CH:30][CH:29]=[CH:36][CH:35]=2)[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20]1.[CH3:38][CH:39]1[C:40]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:33]([C:32]2[CH:35]=[CH:36][C:29]([Cl:28])=[CH:30][CH:31]=2)[CH2:34]1

Participants

7

Reactant 5

HCID 1004Phosphoric AcidHCID 7108PhenothiazineHCID 7501StyreneHCID 140854-ChlorostyreneHCID 2314961-Chloro-2-phenylethane

Product 2

HCID 229241-Methyl-3-phenyl-2,3-dihydro-1H-indeneHCID 21490573HCID 21490573, compound

Conditions

Temperature
40 °C

Procedure

A mixture of 375 parts of phosphoric cid (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, 69 parts of p-chlorostyrene and 61 parts of p-chloroethylbenzene is added to the irradiated solution over 3 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 200 parts of 5 per cent strength by weight sodium hydroxide solution, and fractional distillation gives 18 parts of 1-methyl-3-phenylindan and 72 parts of 1-methyl-3-(p-chlorophenyl)-indan (b.p. 151° to 155° C (4 mm), nD25 : 1.5869).

Workup

  1. customis irradiated for 10 minutes analogously to Example 11
  2. additionis added to the irradiated solution over 3 hours at 35° to 40° C
  3. additionAfter completion of the addition
  4. customThe organic phase is separated off
  5. washwashed with 200 parts of 5 per cent strength by weight sodium hydroxide solution, and fractional distillation

Sources & evidence

ORD record
ord-287432de2f3b48ae9c99569bba7871b8
Source dataset
uspto-grants-1976_12
Patent number
US03998894

Reaction notes

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