Ethanol → HCID 14392659, compound

HRID 1252974Notes

Reaction equation

HRID 1252974 reaction equation
[Na].C([C:4](CC)([C:8]([O-:10])=O)C([O-])=O)C.[CH:13]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26](=[O:28])[CH3:27])=[CH:20][CH:19]=1)=[CH:14][C:15](=[O:17])[CH3:16].[OH-].[K+].[CH2:31]([OH:33])[CH3:32]>O>[C:31]1(=[O:33])[CH2:32][CH:13]([C:18]2[CH:19]=[CH:20][C:21]([CH:24]3[CH2:25][C:26](=[O:28])[CH2:27][C:8](=[O:10])[CH2:4]3)=[CH:22][CH:23]=2)[CH2:14][C:15](=[O:17])[CH2:16]1

Participants

7

Reactant 5

HCID 702EthanolHCID 14797Potassium HydroxideHCID 262615HCID 262615, compoundHCID 5360545SodiumHCID 69515632,2-Diethylpropanedioate

Product 1

HCID 14392659HCID 14392659, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium metal (2.9 g) in absolute ethanol (170 ml) was added diethylmalonate (20.1 g) and then with warming and stirring of the solution, 1,4-bis(but-1-ene-3-one-1-yl)benzene (12.2 g) was added. The mixture was stirred and refluxed for 1.5 hours and then a solution of potassium hydroxide (16.7 g) in water (150 ml) was added and refluxing was continued for 4 hours. Most of the ethanol was removed by distillation and the cooled aqueous residue was washed with ether to remove any organic impurities. The aqueous layer was then heated again and acidified slowly with dilute hydrochloric acid. The precipitated solid was removed by filtration to give 1,4-bis(cyclohexane-1,3-dione-5-yl)benzene (18 g, 100%) as a pale yellow solid, mp >260° C. (dec).

Workup

  1. temperaturewith warming
  2. additionwas added
  3. temperaturerefluxed for 1.5 hours
  4. temperaturerefluxing
  5. customMost of the ethanol was removed by distillation
  6. washthe cooled aqueous residue was washed with ether
  7. customto remove any organic impurities
  8. temperatureThe aqueous layer was then heated again
  9. customThe precipitated solid was removed by filtration

Sources & evidence

ORD record
ord-e348106238c942f7b67fb5d0a6450e4d
Source dataset
uspto-grants-1988_05
Patent number
US04746350

Reaction notes

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