Potassium Hydroxide → HCID 54300978, compound

HRID 1388130Notes

Reaction equation

HRID 1388130 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:22])[CH:7]([CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C>[CH2:3]([O:5][C:6](=[O:22])[CH:7]([CH2:13][CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14030861HCID 14030861, compound

Product 1

HCID 54300978HCID 54300978, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 13.5 g of potassium hydroxide in 160 ml of ethanol is added dropwise in the course of one hour and while stirring to 68 g of (3-cyclohexylpropyl)-malonic acid diethyl ester (prepared analogously to Example 4d), dissolved in 160 ml of ethanol. After stirring for 24 hours at room temperature, the mixture is concentrated considerably in vacuo and the residue is dissolved in 400 ml of water and extracted with 300 ml of diethyl ether. 40 ml of half-concentrated hydrochloric acid are added to the aqueous phase, while cooling with ice, and the mixture is extracted with 3 times 300 ml of diethyl ether. The combined organic phases are dried over sodium sulphate and concentrated. This gives 51 g of (3-cyclohexylpropyl)-malonic acid ethyl ester in the form of a viscous, yellowish oil.

Workup

  1. customprepared analogously to Example 4d),
  2. concentrationthe mixture is concentrated considerably in vacuo
  3. dissolutionthe residue is dissolved in 400 ml of water
  4. extractionextracted with 300 ml of diethyl ether
  5. addition40 ml of half-concentrated hydrochloric acid are added to the aqueous phase
  6. temperaturewhile cooling with ice
  7. extractionthe mixture is extracted with 3 times 300 ml of diethyl ether
  8. dry with materialThe combined organic phases are dried over sodium sulphate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-235414d22e18459c8b334a71c8ed33b8
Source dataset
uspto-grants-1984_02
Patent number
US04430339

Reaction notes

Loading…