Acetic Acid → HCID 22165514, compound

HRID 1032361Notes

Reaction equation

HRID 1032361 reaction equation
[N+](=[CH:3][C:4](=[O:9])[CH2:5][CH2:6][CH:7]=[CH2:8])=[N-].[C:10]([OH:13])(=[O:12])[CH3:11]>>[C:10]([O:13][CH2:3][C:4](=[O:9])[CH2:5][CH2:6][CH:7]=[CH2:8])(=[O:12])[CH3:11]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 573123741-Diazoniohexa-1,5-dien-2-olate

Product 1

HCID 22165514HCID 22165514, compoundYield 90%

Procedure

Into 35 ml of glacial acetic acid at 60°-70° C. is dropped slowly 12.4 g. (0.1 mole) of 1-diazo-5-hexen-2-one. After the nitrogen evolution stops, the reaction mixture is heated to reflux for one hour. The resulting mixture is extracted with 3×50 ml of methylene chloride. The organic layer is dried over anhydrous magnesium sulfate. Concentration of the filtrate gives 1-acetoxy-5-hexen-2-one as a brown oil in 90% yield, based on the starting 4-pentenoyl chloride.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for one hour
  3. extractionThe resulting mixture is extracted with 3×50 ml of methylene chloride
  4. dry with materialThe organic layer is dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-10668798f95048d38a6eaea2ff6e6977
Source dataset
uspto-grants-1990_09
Patent number
US04957912

Reaction notes

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