Hydrochloric Acid → HCID 21527350, compound

HRID 1659181Notes

Reaction equation

HRID 1659181 reaction equation
[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10](=[O:11])[C:9]2[C:4](=[CH:5][C:6]([OH:14])=[C:7]([Cl:13])[C:8]=2[Cl:12])[C:3]1=[O:15].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32]CC)=[O:31].[OH-].[K+].Cl>CN(C)C=O.O.CO>[O:15]=[C:3]1[C:4]2[C:9](=[C:8]([Cl:12])[C:7]([Cl:13])=[C:6]([O:14][CH2:29][C:30]([OH:32])=[O:31])[CH:5]=2)[C:10](=[O:11])[C:2]1([CH3:1])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 21481309HCID 21481309, compound

Product 1

HCID 21527350HCID 21527350, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 2-methyl-2-phenyl-4,5-dichloro-6-hydroxyindan-1,3-dione (2.14 g., 0.0067 mole), potassium carbonate (1.85 g., 0.0134 mole) and ethyl bromoacetate (2.32 g., 0.0134 mole) in dimethylformamide (30 ml.) is warmed at 55°-60°C. for 3 hours, then treated with potassium hydroxide (0.97 g., 0.0147 mole) dissolved in a minimum amount of water in methanol (30 ml.) and heated on a steam bath for 21/2 hrs. The reaction mixture is poured into water (500 ml.), acidified with 6 N hydrochloric acid and the precipitate collected after trituration with ether-petroleum ether and dried to give (1,3-dioxo-2-methyl-2-phenyl-4,5-dichloro-6-indanyloxy)acetic acid.

Workup

  1. temperatureis warmed at 55°-60°C. for 3 hours
  2. temperatureheated on a steam bath for 21/2 hrs
  3. customthe precipitate collected after trituration with ether-petroleum ether
  4. customdried

Sources & evidence

ORD record
ord-e158ae001a23427990f9031116b1ddb2
Source dataset
uspto-grants-1976_06
Patent number
US03966966

Reaction notes

Loading…