Isopropanol → Isopropyl acetoacetate

HRID 845571Notes

Reaction equation

HRID 845571 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH:5]=[C:4]([CH3:9])[O:3]1.CC(O)C>CC(C)=O>[C:6]([O:7][CH:2]([CH3:10])[CH3:1])(=[O:8])[CH2:5][C:4]([CH3:9])=[O:3]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 68329Isopropyl acetoacetateYield 90.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2,2,6-trimethyl-4H-1,3-dioxin-4-one (53)70 (74 g, 0.5 mol) and 2-propanol (30 g, 0.5 mol) was heated at 135° C. for 20 h. The acetone formed during the reaction was removed with a rotary evaporator. The residue was distilled to provide 65 g (0.451 mol, 90%) of 54 as a clear, colorless liquid: bp 185°-187° C.

Workup

  1. customwas removed with a rotary evaporator
  2. distillationThe residue was distilled

Sources & evidence

ORD record
ord-0080dd0dc40f4fbd8b09a373bd10b88e
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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