Sodium hydride → HCID 54179601, compound

HRID 1981921Notes

Reaction equation

HRID 1981921 reaction equation
[OH:1][CH:2]([CH2:11][CH:12]=[CH:13][CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].[CH:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]>CN(C)C=O>[OH:1][C:2]([C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([CH:17]([CH3:18])[CH3:19])=[CH:21][CH:22]=1)([CH2:11][CH:12]=[CH:13][CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 27594864-Isopropylbenzoyl chlorideHCID 56606616HCID 56606616, compound

Product 1

HCID 54179601HCID 54179601, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-3-propenylpropiophenone (2.4 grams) is dissolved in 30 ml of dimethylformamide and 0.6 gram of 50% sodium hydride is added thereto little by little at room temperature with stirring. The mixture is stirred for one hour more at the same temperature and 2.4 grams of p-isopropylbenzoyl chloride is dropped thereinto with ice cooling. The mixture is stirred at room temperature for one hour, 0.6 gram of 50% sodium hydride is added thereto, the mixture is heated at 60° to 70° C. for one hour, cooled, and poured into ice water. This is extracted with ethyl acetate, the extract is washed with water, dried with anhydrous magnesium sulfate, the solvent is evaorated therefrom, and the resulting crystals are washed with n-hexane to give 3.6 grams of 2-hydroxy-3-propenyl-alpha-p-isopropylbenzoylpropiophenone, pale yellow powder, melting point 108° to 110° C.

Workup

  1. additionis dropped
  2. stirringThe mixture is stirred at room temperature for one hour
  3. temperaturethe mixture is heated at 60° to 70° C. for one hour
  4. temperaturecooled
  5. extractionThis is extracted with ethyl acetate
  6. washthe extract is washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. washthe resulting crystals are washed with n-hexane

Sources & evidence

ORD record
ord-d51be88c54ca4c55af4b40dd28e5401e
Source dataset
uspto-grants-1986_06
Patent number
US04594345

Reaction notes

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