Hydrochloric Acid → HCID 21481308, compound

HRID 435773Notes

Reaction equation

HRID 435773 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]([OH:12])[CH:8]=[C:7]2[C:3]=1[CH:4]([OH:18])[C:5]1([CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:6]2[OH:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28].[OH-].[Na+].Cl>CN(C)C=O.O>[OH:13][CH:6]1[C:7]2[C:3](=[C:2]([Cl:1])[C:10]([CH3:11])=[C:9]([O:12][CH2:26][C:27]([OH:29])=[O:28])[CH:8]=2)[CH:4]([OH:18])[C:5]21[CH2:17][CH2:16][CH2:15][CH2:14]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 21481316HCID 21481316, compound

Product 1

HCID 21481308HCID 21481308, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A stirred mixture of 4'-chloro-5'-methylspiro(cyclopentane-1,2'-indan)-1',3',6'-triol (4.0 g., 0.015 mole), potassium carbonate (3.6 g.) and ethyl bromoacetate (3.1 ml.) in dimethylformamide (35 ml.) is heated at 55° C. for one-half hour in an inert atmosphere, treated with water (50 ml.) and 10N sodium hydroxide (5 ml.) then heated at 95° for one-half hour and poured into cold dilute hydrochloric acid affording [1',3'-dihydroxy-4'-chloro-5'-methylspiro(cyclopentane-1,2'-indan)-6'-yloxy]acetic acid.

Workup

  1. temperaturethen heated at 95° for one-half hour

Sources & evidence

ORD record
ord-2db7de6ddeda42ef8b9776250dc7b328
Source dataset
uspto-grants-1977_02
Patent number
US04006180

Reaction notes

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