Ethanol → HCID 69050273, compound

HRID 1455701Notes

Reaction equation

HRID 1455701 reaction equation
C(O)C.[OH-].[K+].C([O:8][C:9](=[O:32])[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][C:18]([CH3:30])([CH3:29])[C:17]2=[O:31])C>O>[CH2:23]([C:22]1[CH:21]=[C:20]2[C:16]([C:17](=[O:31])[C:18]([CH3:30])([CH3:29])[CH2:19]2)=[CH:15][C:14]=1[O:13][CH2:12][CH2:11][CH2:10][C:9]([OH:32])=[O:8])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 69049320HCID 69049320, compound

Product 1

HCID 69050273HCID 69050273, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 60 ml of ethanol, 0.4 g (7.2 mmol) of potassium hydroxide, 1.8 g (4.8 mmol) of ethyl4-(6-hexyl-2,2-dimethyl-3-oxoindan-5-yloxy)butyrate and 20 ml of water is heated for 2 hours 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 1.46 g of product, which is purified by flash chromatography (95/5 dichloromethane/methanol): 1.18 g; m.p.: 82° C.; 71%.

Workup

  1. temperatureis heated for 2 hours 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-b5091936a0984679a087ff46fd1210b8
Source dataset
uspto-grants-2009_01
Patent number
US07482484B2

Reaction notes

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