Hydrochloric Acid → HCID 20378204, compound

HRID 1447680Notes

Reaction equation

HRID 1447680 reaction equation
[C:1]1([C:7]2([CH3:26])[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]3[C:9](=[C:10]([Cl:24])[C:11]([Cl:23])=[C:12]([OH:22])[CH:13]=3)[C:8]2=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37]CC)=[O:36].[OH-].[Na+].Cl>CN(C)C=O.O>[O:25]=[C:8]1[C:9]2[C:14](=[CH:13][C:12]([O:22][CH2:34][C:35]([OH:37])=[O:36])=[C:11]([Cl:23])[C:10]=2[Cl:24])[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]1([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 20378234HCID 20378234, compound

Product 1

HCID 20378204HCID 20378204, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 2,3-diphenyl-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (2.24 g., 0.00585 mole), potassium carbonate (1.62 g., 0.0117 mole) and ethyl bromoacetate (1.96 g., 0.0117 mole) in dimethylformamide (100 ml.) is warmed at 55°-60° C. for 3 hours, then treated with water (100 ml.)-10 N sodium hydroxide solution (5 ml., 0.05 mole) and heated at 90° C. for 1.5 hours. The reaction mixture is added slowly to water (1 l.)-12 N hydrochloric acid (10 ml.) to precipitate 1.14 g. of (1-oxo-2,3-diphenyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 203°-205° C. after crystallization from nitromethane.

Workup

  1. temperatureis warmed at 55°-60° C. for 3 hours
  2. customto precipitate 1.14 g
  3. customof (1-oxo-2,3-diphenyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 203°-205° C. after crystallization from nitromethane

Sources & evidence

ORD record
ord-de534e0372394e81804cb11369f4251d
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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