Malonic Acid → 2,2-Dimethyl-1,3-dioxane-4,6-dione

HRID 2185013Notes

Reaction equation

HRID 2185013 reaction equation
O=[C:2]([CH2:7]CC)[CH2:3]C(O)=O.[C:10]([OH:16])(=[O:15])[CH2:11][C:12]([OH:14])=[O:13].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:3][C:2]1([CH3:7])[O:16][C:10](=[O:15])[CH2:11][C:12](=[O:14])[O:13]1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 4396583-Oxohexanoic acidHCID 517165Ammonium Acetate

Product 1

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneYield 191.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

50 g of resin-bound 2-oxopentanecarboxylic acid (1) are swollen in 200 ml of acetic acid and treated with 20 g of malonic acid (2). 10 g of anhydrous ammonium acetate are added and the mixture is heated to 50° C. After stirring carefully for 3 h, the resin is freed from the solution, washed thoroughly with DMF and methylene chloride and dried. 53 g of (3) are obtained. Removal of a sample using anhydrous TFA yields the free Meldrum's. acid derivative (3, Li-P=H) (HPLC, MS).

Workup

  1. washwashed thoroughly with DMF and methylene chloride
  2. customdried

Sources & evidence

ORD record
ord-b2816eef29404a9b9963b60b8b65e091
Source dataset
uspto-grants-2002_06
Patent number
US06399653B1

Reaction notes

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