Acetone → Dimethyl (propan-2-ylidene)propanedioate

HRID 1974438Notes

Reaction equation

HRID 1974438 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:10][C:11]([CH3:13])=O.O>C(OC(=O)C)(=O)C.[Cl-].[Zn+2].[Cl-]>[C:11](=[C:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])([CH3:13])[CH3:10]

Participants

6

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 7943Dimethyl malonate

Product 1

HCID 5162084Dimethyl (propan-2-ylidene)propanedioate

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 51 grams (0.39 mol) of dimethyl malonate, 30 grams of acetone, and 2.5 grams of zinc chloride in 50 mL of acetic anhydride was refluxed with stirring for 24 hours. The solution was poured into ice and water, then extracted with 200 mL of dichloromethane. The organic phase was washed 2×150 mL water, dried over sodium sulfate and concentrated to a brown oil. After two distillations the 41 gram fraction collected at 25°-34° C. (0.1 mm Hg) gave satisfactory analytical for dimethyl isopropylidenemalonate.

Workup

  1. extractionextracted with 200 mL of dichloromethane
  2. washThe organic phase was washed 2×150 mL water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to a brown oil
  5. distillationAfter two distillations the 41 gram fraction collected at 25°-34° C. (0.1 mm Hg)

Sources & evidence

ORD record
ord-8ec5d3ea36424554b5aca9e8f7f9ab82
Source dataset
uspto-grants-1994_02
Patent number
US05283165

Reaction notes

Loading…