Malonic Acid → 1,3-Dioxane-4,6-dione, 2-methyl-2-(2-phenylethyl)-

HRID 1655509Notes

Reaction equation

HRID 1655509 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].C(OC(=O)C)(=O)C.S(=O)(=O)(O)O.[C:20]1([CH2:26][CH2:27][C:28](=O)[CH3:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[CH3:29][C:28]1([CH2:27][CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:6][C:1](=[O:7])[CH2:2][C:3](=[O:5])[O:4]1

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 17355Benzyl acetone

Product 1

HCID 119757871,3-Dioxane-4,6-dione, 2-methyl-2-(2-phenylethyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of malonic acid (56.7 g, 0.55 mol) and acetic anhydride (73 ml), sulfuric acid (2 ml) was added dropwise at 5°-10° C. and stirring was continued for 20 min at the same temperature. To this mixture, 4-phenyl-2-butanone (105 g, 0.7 mol) was added dropwise at 15°-20° C. and stirring was continued for 15 h at the same temperature. The reaction mixture was taken up into H2O, extracted with chloroform, then the organic extract was washed with H2O, dried over anhydrous MgSO4 and evaporated. The resultant solid was recrystallized from aqueous acetone to give the title compound as a white amorphous solid; yield: 68.0 g; mp. 63.0°-65.0° C.

Workup

  1. stirringstirring
  2. waitwas continued for 15 h at the same temperature
  3. extractionextracted with chloroform
  4. extractionthe organic extract
  5. washwas washed with H2O
  6. dry with materialdried over anhydrous MgSO4
  7. customevaporated
  8. customThe resultant solid was recrystallized from aqueous acetone

Sources & evidence

ORD record
ord-8fa70bbbf4f04ee0959b0faa5a5cbbb4
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

Loading…