Ethanol → HCID 178444492, compound

HRID 1109696Notes

Reaction equation

HRID 1109696 reaction equation
[OH-:1].[K+].C([OH:5])C.[C:6]([CH:8]([C@H:14]1[CH2:19][CH2:18][C@H:17](/[CH:20]=[CH:21]/[CH2:22][CH2:23][CH3:24])[CH2:16][CH2:15]1)[C:9]([O:11]CC)=[O:10])#N>O>[CH:20](/[C@H:17]1[CH2:18][CH2:19][C@H:14]([CH:8]([C:9]([OH:11])=[O:10])[C:6]([OH:5])=[O:1])[CH2:15][CH2:16]1)=[CH:21]\[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 178444482HCID 178444482, compound

Product 1

HCID 178444492HCID 178444492, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 36.9 g of potassium hydroxide, 250 ml of water, 250 ml of ethanol and 37.2 g of ethyl cyano-[trans-4-(1E-pentenyl)cyclohexyl]acetate is heated to boiling for 3 days while stirring. After cooling the reaction mixture is diluted with 500 ml of water and washed with two 200 ml portions of diethyl ether. 220 ml of 10 percent (v/v) sulphuric acid are added dropwise to the aqueous phase. The precipitated product is extracted with three 200 ml portions of diethyl ether. The extract is washed with two 50 ml portions of water, dried over sodium sulphate, filtered and concentrated. Repeated recrystallization from benzene/hexane (vol. 1:1) gives pure [trans-4-(1E-pentenyl)cyclohexyl]malonic acid.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling the reaction mixture
  3. washwashed with two 200 ml portions of diethyl ether
  4. addition220 ml of 10 percent (v/v) sulphuric acid are added dropwise to the aqueous phase
  5. extractionThe precipitated product is extracted with three 200 ml portions of diethyl ether
  6. washThe extract is washed with two 50 ml portions of water
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customrecrystallization from benzene/hexane (vol. 1:1)

Sources & evidence

ORD record
ord-59e6e05ff667449b8dc8f7d75b100f40
Source dataset
uspto-grants-1994_06
Patent number
US05322638

Reaction notes

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