Water → HCID 12252003, compound

HRID 1533496Notes

Reaction equation

HRID 1533496 reaction equation
[C:1]([O:10]CC)(=[O:9])[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13]1(=O)[CH2:18]CCC[CH2:14]1.CC(C)([O-])C.[K+].O>C(O)(C)(C)C>[CH2:7]([O:6][C:4](=[O:5])[C:3](=[C:13]([CH3:18])[CH3:14])[CH2:2][C:1]([OH:10])=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7967CyclohexanoneHCID 31249Diethyl SuccinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 12252003HCID 12252003, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of of 17.4 g (0.1 mol) diethyl succinate and 9.8 g (0.1 mol) cyclohexanone in 100 ml tert-butanol was added 11.2 g (0.1 mol) potassium tert-butoxide in one portion. The mixture was allowed to stir at room temperature for 30 min. 10 ml of water were added and the solvent was removed under reduced pressure. The residue was dissolved in 100 ml water and transferred into a separation funnel. The solution was extracted twice with 50 ml ethyl acetate to remove neutral impurities, acidified with 6M HCl and extracted again twice with 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 18.5 g (82%) of a thick yellow oil. 1H-NMR: 86% conjugated, 14% deconjugated product.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 100 ml water
  3. customtransferred into a separation funnel
  4. extractionThe solution was extracted twice with 50 ml ethyl acetate
  5. customto remove neutral impurities
  6. extractionextracted again twice with 20 ml of ethyl acetate
  7. dry with materialThe combined organic phases were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51be529fe7774d7bb255d5d157fa862a
Source dataset
uspto-grants-2001_03
Patent number
US06207853B1

Reaction notes

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