Acetic Acid → 5-Cyclobutylidene-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 449448Notes

Reaction equation

HRID 449448 reaction equation
[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+].[CH3:11][C:12]1([CH3:20])[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[O:13]1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[C:1]1(=[C:15]2[C:16](=[O:18])[O:17][C:12]([CH3:20])([CH3:11])[O:13][C:14]2=[O:19])[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 517165Ammonium Acetate

Product 1

HCID 594965465-Cyclobutylidene-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Cyclobutanone (0.50 g, 7.1 mmol) (Aldrich, Cat. #C96001) was added to a mixture of ammonium acetate (1.1 g, 14 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (1.0 g, 7.1 mmol) (Acros Organics, Cat. #19845) in toluene (10 mL), followed by acetic acid (1.0 mL). The reaction mixture was stirred at 50° C. for 4 h. After cooled to r.t., the mixture was diluted with water, and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%) to afford the desired product (0.68, 48%).

Workup

  1. temperatureAfter cooled to r.t.
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%)

Sources & evidence

ORD record
ord-268592c2631448468428b246fc64853b
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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