Allyl Alcohol → Allyl acetoacetate

HRID 1723451Notes

Reaction equation

HRID 1723451 reaction equation
[CH2:1](O)[CH:2]=[CH2:3].[C:5]([O-:8])(=[O:7])[CH3:6].[Na+].C=C1O[C:13](=[O:14])[CH2:12]1>O1CCOCC1>[C:5]([O:8][CH2:1][CH:2]=[CH2:3])(=[O:7])[CH2:6][C:13]([CH3:12])=[O:14]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 12661DiketeneHCID 517045Sodium Acetate

Product 1

HCID 70701Allyl acetoacetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A one liter reaction vessel equipped with a thermometer, a condenser and a dropping funnel was charged with 58 g (1 mol) of allyl alcohol, 100 g of dioxane and 0.41 g of sodium acetate (catalyst) under nitrogen blanket and heated to 60° C., to which 84 g (1 mol) of diketene was added dropwise for one hour. After completion of the addition, it was allowed to react for 2 hours with heating and dioxane was removed at a reduced pressure. The reaction product was further distilled to obtain 2-propenyl acetoacetate. It was identified by absorption at 1,742, 1,721 and 1,684 cm-1 in IR spectrum.

Workup

  1. customA one liter reaction vessel
  2. customequipped with a thermometer, a condenser and a dropping funnel
  3. additionwas added dropwise for one hour
  4. additionAfter completion of the addition, it
  5. customto react for 2 hours
  6. temperaturewith heating
  7. customdioxane was removed at a reduced pressure
  8. distillationThe reaction product was further distilled

Sources & evidence

ORD record
ord-6c4a6aef2ee74348a4d950edae9199e6
Source dataset
uspto-grants-1989_08
Patent number
US04861839

Reaction notes

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