Potassium Carbonate → 4-(1-Oxo-2-ethyl-6,7-dichloro-5-indanyloxy)-butyric Acid

HRID 1834699Notes

Reaction equation

HRID 1834699 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][CH:7]([CH2:13][CH3:14])[C:8]2=[O:12])=[CH:4][C:3]=1[OH:15].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27].[OH-].[K+]>CN(C)C=O.CO.O>[O:12]=[C:8]1[C:9]2[C:5](=[CH:4][C:3]([O:15][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[C:2]([Cl:1])[C:10]=2[Cl:11])[CH2:6][CH:7]1[CH2:13][CH3:14]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 76300Ethyl 4-bromobutyrateHCID 128572202-Ethyl-5-hydroxy-6,7-dichloroindanone

Product 1

HCID 203739044-(1-Oxo-2-ethyl-6,7-dichloro-5-indanyloxy)-butyric Acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6,7-Dichloro-2-ethyl-5-hydroxy-1-indanone (24.5 g., 0.1 mole) and anhydrous potassium carbonate (15.2 g., 0.11 mole) is stirred in dimethylformamide (100 ml.) while ethyl 4-bromobutyrate (21.4 g., 0.1 mole) is added dropwise. The mixture is stirred and heated at 55°-60° C. for two hours. Potassium hydroxide (7.92 g., 0.141 mole) in methanol (60 ml.) is then added. The solid mass that forms is broken up and the mixture is stirred at 80°-85° C. for 11/2 hours and poured into water (500 ml.). The aqueous mixture is heated to boiling, filtered and acidified (6N HCl). The solid that separates is collected, washed with water, air-dried and recrystallized from ethylacetate to obtain 25.6 g. of 4-(1(1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)butyric acid, m.p. 146°-148° C.

Workup

  1. additionis added dropwise
  2. temperatureheated at 55°-60° C. for two hours
  3. stirringthe mixture is stirred at 80°-85° C. for 11/2 hours
  4. temperatureThe aqueous mixture is heated
  5. filtrationfiltered
  6. customThe solid that separates is collected
  7. washwashed with water
  8. customair-dried
  9. customrecrystallized from ethylacetate
  10. customto obtain 25.6 g

Sources & evidence

ORD record
ord-c84bbac34a7e4a3088fd02379803e0d5
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

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