Ethanol → Ethyl 3-oxo-3-[4-(propan-2-yl)phenyl]propanoate

HRID 986232Notes

Reaction equation

HRID 986232 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=1)([CH3:11])[CH3:10].[CH2:21](O)C>CCOCC>[CH:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH2:19][C:3]([O:6][CH2:7][CH3:21])=[O:8])=[O:20])=[CH:14][CH:13]=1)([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 12021Dimethyl CarbonateHCID 125784-IsopropylacetophenoneHCID 24758Sodium hydride

Product 1

HCID 2759504Ethyl 3-oxo-3-[4-(propan-2-yl)phenyl]propanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium hydride (2.4 grams) and 4.5 grams of dimethyl carbonate are suspended in 150 ml of ether. 8.1 grams of p-isopropylacetophenone is gradually dropped thereinto under heating to reflux, then a small amount of ethanol is added thereto, heated to reflux for one hour, cooled, and the reaction is stopped by the addition of 20 ml of ethanol. The mixture is poured into ice water and extracted with ether. The ether extracts are combined, washed with water, dried with anhydrous magnesium sulfate and ether is evaporated therefrom. The resulting oil is purified by distillting in vacuo to give 6.5 grams of colorless oily product, b.p. 80° C./5 mmHg.

Workup

  1. temperatureunder heating
  2. temperatureto reflux
  3. temperatureheated
  4. temperatureto reflux for one hour
  5. temperaturecooled
  6. extractionextracted with ether
  7. washwashed with water
  8. dry with materialdried with anhydrous magnesium sulfate and ether
  9. customis evaporated
  10. customThe resulting oil is purified

Sources & evidence

ORD record
ord-dfcace238e5443929929d718f82ad1c5
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

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