Acetone → 2,2-Dimethyl-1,3-dioxane-4,6-dione

HRID 462036Notes

Reaction equation

HRID 462036 reaction equation
S(=O)(=O)(O)O.[C:6]([OH:12])(=[O:11])[CH2:7][C:8]([OH:10])=[O:9].C(OC(=O)C)(=O)C.[CH3:20][C:21]([CH3:23])=O>>[C:6]1(=[O:12])[O:11][C:21]([CH3:23])([CH3:20])[O:10][C:8](=[O:9])[CH2:7]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 867Malonic AcidHCID 1118Sulfuric AcidHCID 7918Acetic Anhydride

Product 1

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneYield 44.4%

Procedure

The diisopropylidene methylene dimalonate used in this Example was prepared by adding 1.5 ml concentrated sulfuric acid over a 20 minute period to a stirred slurry of 52 grams malonic acid (0.5 mol) and 60 ml acetic anhydride (0.6 mol) in an erlenmeyer flask reactor. After the reactants were stirred for 3 hours at room temperature, 40 ml acetone (0.55 mols) were added with cooling and the reactants were maintained at 5° C for 16 hours. The crystalline product was filtered, washed with ice water and dried yielding 32 grams isopropylidene malonate having a melting point of 97°-98° C. A solution of 14.4 grams of isopropylidene malonate (0.1 mol), 4.0 grams of 37% aqueous formaldehyde (0.05 mol) and 40 ml dimethyl formamide was maintained at room temperature for 3 hours in an erlenmeyer flask. After the addition of 25 ml water, white crystals precipitated from the dimethyl formamide. The crystals were washed with water and dried yielding 10 grams of diisopropylidene methylene dimalonate which melted at from 152°-153° C.

Workup

  1. customwas prepared
  2. temperaturewith cooling
  3. temperaturethe reactants were maintained at 5° C for 16 hours
  4. filtrationThe crystalline product was filtered
  5. washwashed with ice water
  6. customdried

Sources & evidence

ORD record
ord-268759421058481daa04fdeb16f62d68
Source dataset
uspto-grants-1977_12
Patent number
US04065440

Reaction notes

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