Cyclohexanecarboxaldehyde → HCID 66715341, compound

HRID 1533494Notes

Reaction equation

HRID 1533494 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:16]CC)(=[O:15])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:19]1[CH2:24][CH2:23][CH:22]([CH:25]=O)[CH2:21][CH2:20]1>C(O)(C)(C)C>[CH2:13]([O:12][C:10](=[O:11])[C:9](=[CH:25][CH:22]1[CH2:23][CH2:24][CH2:19][CH2:20][CH2:21]1)[CH2:8][C:7]([OH:16])=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 31249Diethyl SuccinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 66715341HCID 66715341, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 11.2 g (0.1 mol) potassium tert-butoxide in 100 ml tert-butanol was added a mixture of 17.4 g (0.1 mol) diethyl succinate and 11.2 g (0.1 mol) cyclohexylcarboxaldehyde over a period of 30 min. The mixture was allowed to stir at room temperature for one hour and heated to 50° C. for an additional hour. 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 18.9 g (79%) of a yellow brown oil. 1H-NMR: 66% E-isomer, 13% Z-isomer, 15% cyclohexenyl-isomer, 6% other unsaturated olefelinic compound.

Workup

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

Sources & evidence

ORD record
ord-5c7140242a364ecb8dc6607d42bdd0c7
Source dataset
uspto-grants-2001_03
Patent number
US06207853B1

Reaction notes

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