Diethyl Ether → HCID 53801870, compound

HRID 582617Notes

Reaction equation

HRID 582617 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11](Cl)(=[O:15])[CH2:12][CH2:13][CH3:14].C([O:19]CC)C>N1C=CC=CC=1>[C:11]([O:15][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:3](=[O:4])[CH3:2])(=[O:19])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8855Butyryl chlorideHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 53801870HCID 53801870, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 50 g (367 mmol) of 2-hydroxyacetophenone and 47 g (440 mmol) of butyryl chloride in 100 ml of pyridine is stirred for 30 minutes, then diluted with diethyl ether and washed successively with water and aqueous hydrochloric acid. The organic phase is then dried over sodium sulfate, concentrated under reduced pressure and coevaporated 3 times with toluene. By chromatography of the residue on a silica column using a 0-30% mixture of ethyl acetate in cyclohexane, 72 g of product are obtained in oil form.

Workup

  1. washwashed successively with water and aqueous hydrochloric acid
  2. dry with materialThe organic phase is then dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customare obtained in oil form

Sources & evidence

ORD record
ord-1c163c66ebbb4beba231b4887a18b2d8
Source dataset
uspto-grants-1999_07
Patent number
US05925662

Reaction notes

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