Hydrochloric Acid → HCID 12423607, compound

HRID 1447682Notes

Reaction equation

HRID 1447682 reaction equation
[CH:1]1([C:6]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C:13]3[C:8](=[C:9]([Cl:17])[C:10]([Cl:16])=[C:11]([OH:15])[CH:12]=3)[C:7]2=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][C:33]([O:35]CC)=[O:34].[OH-].[Na+].Cl>CN(C)C=O.O>[O:18]=[C:7]1[C:8]2[C:13](=[CH:12][C:11]([O:15][CH2:32][C:33]([OH:35])=[O:34])=[C:10]([Cl:16])[C:9]=2[Cl:17])[CH2:14][C:6]1([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12423598HCID 12423598, compound

Product 1

HCID 12423607HCID 12423607, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 2-cyclopentyl-2-phenyl-5-hydroxy-6,7-dichloro-1-indanone (1.10 g., 0.003 mole), potassium carbonate (0.85 g., 0.006 mole) and ethyl bromoacetate (1.02 g., 0.006 mole) in dimethylformamide (20 ml.) is warmed at 55°-60° C. for 3 hours, then treated with water (20 ml.)-10 N sodium hydroxide solution (1.2 ml., 0.012 mole) and heated at 100° C. for one hour. The reaction mixture is added slowly to water (300 ml.)-12 N hydrochloric acid (5 ml.) to precipitate 680 mg. of (1-oxo-2-cyclopentyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 184°-186° C. after crystallization from nitromethane.

Workup

  1. temperatureis warmed at 55°-60° C. for 3 hours
  2. customto precipitate 680 mg
  3. customof (1-oxo-2-cyclopentyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 184°-186° C. after crystallization from nitromethane

Sources & evidence

ORD record
ord-ab0884290d0c45c49fe4c5a09c31f373
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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