Acetone → Diethyl 2,2-dimethyl-1,3-dioxane-5,5-dicarboxylate

HRID 1074880Notes

Reaction equation

HRID 1074880 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([CH2:13][OH:14])([CH2:11][OH:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].P(=O)(O)(O)O.[CH3:21][C:22]([CH3:24])=O>C1C=CC=CC=1>[CH3:21][C:22]1([CH3:24])[O:12][CH2:11][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:13][O:14]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 1004Phosphoric AcidHCID 311844Propanedioic acid, 2,2-bis(hydroxymethyl)-, 1,3-diethyl ester

Product 1

HCID 287722Diethyl 2,2-dimethyl-1,3-dioxane-5,5-dicarboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To diethyl-bis-(hydroxymethyl)malonate (50 g) in acetone (50 ml) and benzene (200 ml) is added phosphoric acid (10 g). . The mixture is refluxed while stirring and separating water which distills. When water evolution is complete, the reaction mixture is cooled and the organic layer is separated, stirred with solid sodium carbonate (10 g), filtered and evaporated to give the title product (52 g) (87%) nD26 1.4412.

Workup

  1. temperatureThe mixture is refluxed
  2. customseparating water which
  3. distillationdistills
  4. temperaturethe reaction mixture is cooled
  5. customthe organic layer is separated
  6. stirringstirred with solid sodium carbonate (10 g)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-976e35f5e3e14366b0341fd8b2ef8e90
Source dataset
uspto-grants-1983_07
Patent number
US04394329

Reaction notes

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