Hydrochloric Acid → 2-Phenyl-5-hydroxy-6,7-dichloro-1-indanone

HRID 1156199Notes

Reaction equation

HRID 1156199 reaction equation
[C:1]1([CH:7]2[CH2:15][C:14]3[C:9](=[C:10]([Cl:19])[C:11]([Cl:18])=[C:12]([O:16]C)[CH:13]=3)[C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.N1C=CC=CC=1.Cl>>[C:1]1([CH:7]2[CH2:15][C:14]3[C:9](=[C:10]([Cl:19])[C:11]([Cl:18])=[C:12]([OH:16])[CH:13]=3)[C:8]2=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 109904442-Phenyl-5-methoxy-6,7-dichloro-1-indanone

Product 1

HCID 127740892-Phenyl-5-hydroxy-6,7-dichloro-1-indanoneYield 75%

Procedure

A stirred mixture of 2-phenyl-5-methoxy-6,7-dichloro-1-indanone (5.18 g., 16.8 mmol) and pyridine hydrochloride (23.3 g., 202 mmol) is heated at 190° for a period of 2 hrs. and then poured into 300 ml. of cold 2 N hydrochloric acid. Insolubles are collected, dried and crystallized from ethanol to afford 3.7 g. (75% yield) of 2-phenyl-5-hydroxy-6,7-dichloro-1-indanone, m.p. 252°-253.5°.

Workup

  1. temperatureis heated at 190° for a period of 2 hrs
  2. additionand then poured into 300 ml
  3. customInsolubles are collected
  4. customdried
  5. customcrystallized from ethanol
  6. customto afford 3.7 g

Sources & evidence

ORD record
ord-6ce0523f465848d69403e76daf828945
Source dataset
uspto-grants-1982_06
Patent number
US04334088

Reaction notes

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