Hydrochloric Acid → HCID 12395623, compound

HRID 1287476Notes

Reaction equation

HRID 1287476 reaction equation
[CH2:1]([C:3]1([CH3:22])[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[C:6]([Cl:20])[C:7]([Cl:19])=[C:8]([OH:18])[CH:9]=2)[C:4]1=[O:21])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33]CC)=[O:32].[OH-].[Na+].Cl>CN(C)C=O.O>[O:21]=[C:4]1[C:5]2[C:10](=[CH:9][C:8]([O:18][CH2:30][C:31]([OH:33])=[O:32])=[C:7]([Cl:19])[C:6]=2[Cl:20])[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]1([CH2:1][CH3:2])[CH3:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12395665HCID 12395665, compound

Product 1

HCID 12395623HCID 12395623, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 2-ethyl-2-methyl-3-phenyl-6,7-dichloro-5-hydroxy-1-indanone (6.24 g., 0.0186 mole), potassium carbonate (5.15 g., 0.0372 mole) and ethyl bromoacetate (6.22 g., 0.0372 mole) in dimethylformamide (60 ml.) is warmed at 55°-60° C. for 3 hours, then treated with water (60 ml.) and 10N sodium hydroxide solution (5 ml., 0.05 mole) and heated at 80°C. for one hour. The reaction mixture is added slowly to water (800 ml.)-6N hydrochloric acid (20 ml.) to precipitate (1-oxo-2-ethyl-2-methyl-3-phenyl-6,7-dichloro-5-indanyloxy)acetic acid (3.7 g.) which melts at 192° C. on crystallization from

Workup

  1. temperatureis warmed at 55°-60° C. for 3 hours
  2. customto precipitate (1-oxo-2-ethyl-2-methyl-3-phenyl-6,7-dichloro-5-indanyloxy)acetic acid (3.7 g.) which melts at 192° C.
  3. customon crystallization from

Sources & evidence

ORD record
ord-5a8787cc51394215ab7b854b4af92e37
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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