Ethanol → HCID 15169783, compound

HRID 2165461Notes

Reaction equation

HRID 2165461 reaction equation
[H-].[Na+].C(O)C.[CH3:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[O:8].[C:17](OCC)(=[O:20])[CH2:18][CH3:19]>CCCCCC.C(OCC)C.O>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7](=[O:8])[CH2:6][C:17](=[O:20])[CH2:18][CH3:19])=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 74764'-MethoxyacetophenoneHCID 7749Ethyl PropionateHCID 24758Sodium hydride2×

Product 1

HCID 15169783HCID 15169783, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a suspension of 8.8 g (0.18 mole) of a 50% dispersion of sodium hydride in hexane was added 1 ml of ethanol followed by the addition, over a period of five minutes, of a solution of 30 g (0.2 mole) of 4-methoxyacetophenone in 50 ml of diethyl ether 50 ml of ethyl propionate was then added rapidly, and the solution was heated under reflux for three hours and then cooled. An additional 7 g of sodium hydride dispersion was added, the reaction was allowed to subside, and the mixture was then cooled and diluted with 500 ml of water with stirring. The solid which separated was collected by filtration, washed with water, then with diethyl ether and dried in a vacuum oven at 60° C. to give 18.3 g of 5-(4-methoxyphenyl)-3,5-pentanedione as the sodium salt.

Workup

  1. additionwas then added rapidly
  2. temperaturethe solution was heated
  3. temperatureunder reflux for three hours
  4. temperaturecooled
  5. temperaturethe mixture was then cooled
  6. customThe solid which separated
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. dry with materialwith diethyl ether and dried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-38b01e177d8946fe97ade4dc2effcc64
Source dataset
uspto-grants-1990_07
Patent number
US04939138

Reaction notes

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