Diketene → (2-Methyl-1,3-dioxolan-2-yl)methyl 3-oxobutanoate

HRID 543552Notes

Reaction equation

HRID 543552 reaction equation
[CH2:1]1[CH2:8][O:7][C:3]([CH3:6])([CH2:4][OH:5])[O:2]1.[CH2:9]=[C:10]1[O:14][C:12](=[O:13])[CH2:11]1>[H-].[Na+].C1C=CC=CC=1>[C:12]([O:5][CH2:4][C:3]1([O:7][CH2:8][CH2:1][O:2]1)[CH3:6])(=[O:13])[CH2:11][C:10]([CH3:9])=[O:14]

Participants

5

Reactant 2

HCID 12661DiketeneHCID 12384726(2-Methyl-1,3-dioxolan-2-yl)methanol

Product 1

HCID 13239718(2-Methyl-1,3-dioxolan-2-yl)methyl 3-oxobutanoateYield 70%

Reagents, catalysts & solvents 2

HCID 24758Sodium hydrideCatalystHCID 241BenzeneSolvent

Procedure

100 mg of 50% sodium hydride was added to a mixture of 20 g of 2,2-ethylenedioxypropanol and 100 ml of benzene, and 20 g of diketene was added dropwise to the mixture while refluxing the mixture. After refluxing the mixture for 2 hours, the solvent was distilled off and the resulting residue was distilled under reduced pressure to obtain 21.5 g (70% yield) of 2,2-ethylenedioxypropyl acetoacetate as a colorless oil having a boiling point of 90° C. (6 mmHg).

Workup

  1. additionwas added dropwise to the mixture
  2. temperaturewhile refluxing the mixture
  3. temperatureAfter refluxing the mixture for 2 hours
  4. distillationthe solvent was distilled off
  5. distillationthe resulting residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-29ef256f37f84d0aa14bb3e2588784bb
Source dataset
uspto-grants-1984_05
Patent number
US04446325

Reaction notes

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