Ethanol → HCID 69048864, compound

HRID 1455698Notes

Reaction equation

HRID 1455698 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=[CH2:29])C>O>[CH2:29]=[C:17]1[C:16]2[C:20](=[CH:21][C:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:14]([O:13][CH2:12][CH2:11][CH2:10][C:9]([OH:30])=[O:8])[CH:15]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 69049226HCID 69049226, compound

Product 1

HCID 69048864HCID 69048864, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20 ml of ethanol, 0.975 mg (155 mmol) of potassium hydroxide, 1.2 g (35 mmol) of ethyl4-(3-methylene-6-hexylindan-5-yloxy)butyrate and 10 ml of water is heated for 5 hours at the reflux point of the solvents. The ethanol is evaporated off, the residue is taken up in water and the impurities are extracted with ether. The aqueous phase is acidified and then extracted with ether. Concentration of the solvents gives 1.1 g of product, which is purified by flash chromatography (50/50 heptane/ethyl acetate) to give a solid m.p.: 90° C. (0.8 g; 72%).

Workup

  1. temperatureis heated for 5 hours at the reflux point of the solvents
  2. customThe ethanol is evaporated off
  3. extractionthe impurities are extracted with ether
  4. extractionextracted with ether

Sources & evidence

ORD record
ord-9488438636ff4ce7bde51872d429f669
Source dataset
uspto-grants-2009_01
Patent number
US07482484B2

Reaction notes

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