Malonic Acid → HCID 12667864, compound

HRID 1154759Notes

Reaction equation

HRID 1154759 reaction equation
[CH3:1][C:2]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([CH3:18])[CH:10]=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=[O:6].[C:19](O)(=O)CC(O)=O.C([O-])(=O)C.[Na+].C1(=O)OC(=O)C2=CC=CC=C12>C(O)(=O)C>[CH3:18][C:11]1[CH:10]=[C:4]2[C:3](=[C:2]([CH3:1])[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8](=[O:9])[O:7][C:5]2([OH:6])[CH3:19]

Participants

6

Reactant 4

HCID 867Malonic Acid2×HCID 6811Phthalic AnhydrideHCID 517045Sodium AcetateHCID 12667863HCID 12667863, compound

Product 1

HCID 12667864HCID 12667864, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 500 ml. three-necked glass flask equipped with a reflux condenser, a thermometer and a stirrer was charged with a mixture consisting of 50 g of 3,5-dimethyl-4-ethoxycarbonyl-phthalic anhydride, 42 g of well-dried malonic acid, 30 g of sodium acetate and 200 g of acetic acid, and the flask was heated in an oil bath. The phthalic anhydride derivative was reacted with malonic acid at 90° to 95° C. for 15 hours with stirring. After the reaction, the reaction mixture was analyzed by high-speed liquid chromatography. It was found that the conversion was 90%, and the desired 5,7-dimethyl-6-ethoxycarbonyl-3-hydroxy-3-methylphthalide was obtained in a yield of 77%.

Workup

  1. customthree-necked glass flask equipped with a reflux condenser
  2. additiona thermometer and a stirrer was charged with a mixture
  3. temperaturethe flask was heated in an oil bath
  4. customAfter the reaction

Sources & evidence

ORD record
ord-40a271c915924f73b6c89b2b4e968ffe
Source dataset
uspto-grants-1981_11
Patent number
US04298530

Reaction notes

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