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

HRID 1973858Notes

Reaction equation

HRID 1973858 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[CH2:14].ClCCC1C=CC=CC=1.P(=O)(O)(O)O>>[CH3:14][CH:13]1[C:12]2[C:11](=[CH:10][CH:17]=[CH:16][CH:15]=2)[CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:1]1

Participants

5

Reactant 4

HCID 1004Phosphoric AcidHCID 7501StyreneHCID 14905m-ChlorostyreneHCID 2314961-Chloro-2-phenylethane

Product 1

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

Procedure

A solution containing 90 parts of styrene, 174 parts of m-chlorostyrene and 126 parts of m-chloroethylbenzene is added to 722 parts of 93 per cent strength by weight phosphoric acid at 35° to 40° C over 5 hours. After completion of the addition, the emulsion is stirred for 2 hours at 35° to 40° C. The organic phase is separated off and washed with 200 parts of 3 per cent strength by weight sodium hydroxide solution. Fractional distillation gives 27 parts of 1-methyl-3-phenylindan, 71 parts of 1-methyl-3-(m-chloro)-phenylindan (b.p. 168° to 172° C (10 mm), nD25 : 1.5872) and 23 parts of 1-methyl-3-(m-chloro)-phenyl-6-chloroindan (b.p. 197° to 204° C (10 mm)).

Workup

  1. additionAfter completion of the addition
  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

Sources & evidence

ORD record
ord-d6bf52af883e413ca8412af3c30d8566
Source dataset
uspto-grants-1976_12
Patent number
US03998894

Reaction notes

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