Hydrochloric Acid → [(6,7-Dichloro-2-ethyl-2-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]acetic acid

HRID 1679700Notes

Reaction equation

HRID 1679700 reaction equation
[CH2:1]([C:3]1([CH3:16])[CH2:11][C:10]2[C:5](=[C:6]([Cl:14])[C:7]([Cl:13])=[C:8]([OH:12])[CH:9]=2)[C:4]1=[O:15])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27]CC)=[O:26].[OH-].[Na+].Cl>CN(C=O)C.O>[O:15]=[C:4]1[C:5]2[C:10](=[CH:9][C:8]([O:12][CH2:24][C:25]([OH:27])=[O:26])=[C:7]([Cl:13])[C:6]=2[Cl:14])[CH2:11][C:3]1([CH2:1][CH3:2])[CH3:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12395584HCID 12395584, compound

Product 1

HCID 41028[(6,7-Dichloro-2-ethyl-2-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A stirred mixture of 2-ethyl-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (3.6 g., 0.014 mole), potassium carbonate (4.2 g.), ethyl bromoacetate (5.0 g.) in DMF (40 ml.) is warmed in an inert atmosphere at 55° C. for 1 hour, then treated with water (40 ml.) and 10N sodium hydroxide (6 ml.) and heated on a steam bath for 11/2 hours. The reaction mixture is poured into dilute aqueous hydrochloric acid, extracted with ether, washed with water and dried over magnesium sulfate. The ether is evaporated at reduced pressure affording the crude product which melts at 168° C. after recrystallization from nitromethane.

Workup

  1. temperatureheated on a steam bath for 11/2 hours
  2. extractionextracted with ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe ether is evaporated at reduced pressure

Sources & evidence

ORD record
ord-c00910fc856e4f599458837b128ff85c
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

Loading…