Hydrochloric Acid → HCID 21449493, compound

HRID 596998Notes

Reaction equation

HRID 596998 reaction equation
[CH:1]1([C:6]2([CH3:19])[CH2:14][C:13]3[C:8](=[C:9]([Cl:17])[C:10]([Cl:16])=[C:11]([OH:15])[CH:12]=3)[CH:7]2[OH:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].C([O:28][C:29](=[O:32])[CH2:30]Br)C.[OH-].[Na+].Cl>CN(C)C=O.O>[OH:18][CH:7]1[C:8]2[C:13](=[CH:12][C:11]([O:15][CH2:30][C:29]([OH:32])=[O:28])=[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)[CH3:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 21449489HCID 21449489, compound

Product 1

HCID 21449493HCID 21449493, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 2-cyclopentyl-2-methyl-6,7-dichloroindan-1,5-diol (α isomer) (1.9 g., 0.0063 mole), potassium carbonate (1.3 g., 0.0095 mole) and ethylbromoacetate (1.5 g. 0.0095 mole) in dimethylformamide (20 ml.) is warmed at 55°-60° C. under nitrogen for 2 hours, then treated with water (20 ml.) and 10N sodium hydroxide (1.9 ml.) and heated on a steam bath for one-half hour. The reaction mixture is poured into ice water (300 ml.) and while ice cold, 1N HCl is added dropwise with stirring to give 1.36 g. of (1-hydroxy-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid (α isomer) which melts at 129°-131° C. after crystallization from benzene : hexane, 1:1.

Workup

  1. temperatureis warmed at 55°-60° C. under nitrogen for 2 hours
  2. temperatureheated on a steam bath for one-half hour
  3. additionis added dropwise
  4. customto give 1.36 g
  5. customof (1-hydroxy-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid (α isomer) which melts at 129°-131° C. after crystallization from benzene

Sources & evidence

ORD record
ord-42915d7b79f6479abfa489690061b192
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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