Ethanol → HCID 10087256, compound

HRID 1455696Notes

Reaction equation

HRID 1455696 reaction equation
C(O)C.[OH-].[K+].C([O:8][C:9](=[O:30])[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:19][CH2:18][C:17]2=[O:29])C>O>[CH2:23]([C:22]1[CH:21]=[C:20]2[C:16]([C:17](=[O:29])[CH2:18][CH2:19]2)=[CH:15][C:14]=1[O:13][CH2:12][CH2:11][CH2:10][C:9]([OH:30])=[O:8])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 11858598HCID 11858598, compound

Product 1

HCID 10087256HCID 10087256, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 70 ml of ethanol, 2.7 g (0.048 mol) of potassium hydroxide, 5.9 g (0.017 mol) of ethyl4-(6-hexyl-3-oxoindan-5-yloxy)butyrate and 35 ml of water is heated for 90 minutes at the reflux point of the solvents. The solvents are evaporated off and the residue is placed in water and extracted with ether. The aqueous phase is acidified and then extracted with ether. Concentration of the solvents gives 3.6 g of product, which is purified by flash chromatography (80/20 cyclohexane/ethyl acetate): 1.5 g of crude product. Recrystallisation from hexane gives 1.3 g, m.p. 88° C., 24%.

Workup

  1. temperatureis heated for 90 minutes at the reflux point of the solvents
  2. customThe solvents are evaporated off
  3. extractionextracted with ether
  4. extractionextracted with ether

Sources & evidence

ORD record
ord-381181b75a9c4c038df90879fbb593dd
Source dataset
uspto-grants-2009_01
Patent number
US07482484B2

Reaction notes

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