Phosphoric Acid → HCID 21490574, compound

HRID 1973863Notes

Reaction equation

HRID 1973863 reaction equation
P(=O)(O)(O)O.C1(NC(N)=S)C=CC=CC=1.P(Cl)(Cl)([Cl:18])=O.[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[CH2:27])=[CH:24][CH:23]=1.Cl[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>[Hg]>[CH3:27][CH:26]1[C:25]2[C:24](=[CH:23][C:22]([Cl:21])=[CH:29][CH:28]=2)[CH:32]([C:33]2[CH:38]=[CH:37][C:36]([Cl:18])=[CH:35][CH:34]=2)[CH2:31]1

Participants

7

Reactant 5

HCID 1004Phosphoric AcidHCID 140854-ChlorostyreneHCID 24813Phosphorus oxychlorideHCID 2314961-Chloro-2-phenylethaneHCID 676454Phenylthiourea

Product 1

HCID 21490574HCID 21490574, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 23931MercuryCatalyst

Procedure

200 parts of 98 per cent strength by weight aqueous phosphoric acid containing 0.9 part of phenylthiourea are irradiated for 10 minutes at 25° with ultraviolet light (mercury vapor lamp, with 15 watt hours per kilogram of halogenostyrene III) whilst passing 2,000 parts of air through the mixture. 70 parts of phosphorus oxychloride are added followed by a mixture of 120 arts of p-chlorostyrene and 97 parts of o-chloroethylbenzene added over 3 hours. Distillation of the organic phase gives 97 parts (= 80.7% of theory) of 1-methyl-3-(p-chlorophenyl)-5-chloroindan of b.p. 148° to 156° C (0.15 mm).

Workup

  1. additionadded over 3 hours
  2. distillationDistillation of the organic phase

Sources & evidence

ORD record
ord-e91bdd09f3c44426905dfd94d8275aaf
Source dataset
uspto-grants-1976_12
Patent number
US03998894

Reaction notes

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