Hydrochloric Acid → HCID 12423608, compound

HRID 1447679Notes

Reaction equation

HRID 1447679 reaction equation
[C:1]1([C:7]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][C:14]3[C:9](=[C:10]([Cl:18])[C:11]([Cl:17])=[C:12]([OH:16])[CH:13]=3)[C:8]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36]CC)=[O:35].[OH-].[Na+].Cl>CN(C)C=O.O>[O:19]=[C:8]1[C:9]2[C:14](=[CH:13][C:12]([O:16][CH2:33][C:34]([OH:36])=[O:35])=[C:11]([Cl:17])[C:10]=2[Cl:18])[CH2:15][C:7]1([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12423599HCID 12423599, compound

Product 1

HCID 12423608HCID 12423608, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 2,2-diphenyl-5-hydroxy-6,7-dichloro-1-indanone (4.9 g., 0.0133 mole), potassium carbonate (3.68 g., 0.0266 mole) and ethyl bromoacetate (4.45 g., 0.0266 mole) in dimethylformamide (150 ml.) is warmed at 55°-60° C. for 3.5 hours, then treated with water (150 ml.)-10 N sodium hydroxide solution (7.5 ml., 0.075 mole) and heated at 90° C. for 1.5 hrs. The reaction mixture is added slowly to water (1 l.)-12 N hydrochloric acid (30 ml.) to precipitate 3.60 g. of (1-oxo-2,2-diphenyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 251°-252° C. after crystallization from first acetic acid, then nitromethane.

Workup

  1. temperatureis warmed at 55°-60° C. for 3.5 hours
  2. customto precipitate 3.60 g
  3. customof (1-oxo-2,2-diphenyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 251°-252° C. after crystallization from first acetic acid

Sources & evidence

ORD record
ord-5f4feceb31b4486196e4161270f95dc4
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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