Methanol → HCID 14075270, compound

HRID 986563Notes

Reaction equation

HRID 986563 reaction equation
CO.S(=O)(=O)(O)O.[CH:8]([O:13][CH3:14])([O:11]C)OC.[C:15]([C:23]1C(=O)[O:25][C:26]([CH3:30])=[CH:27][C:28]=1[OH:29])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH3:14][O:13][C:8]([C:23]1[C:28](=[O:29])[CH:27]=[C:26]([CH3:30])[O:25][C:15]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 135472552HCID 135472552, compound

Product 1

HCID 14075270HCID 14075270, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask fitted with a reflux condenser and calcium chloride drying tube is charged with 70 ml dry methanol, 7.3 g of 96% sulfuric acid and 10.15 g of trimethyl orthoformate. 3-Benzoyl-4-hydroxy-6-methyl-2-pyrone (22 g) is then added in small portions and the resulting reaction mixture is refluxed for 24 hours. The mixture is cooled and poured into water. Extraction with methylene chloride yields 17.7 g of crude 3-methoxycarbonyl-6-methyl-2-phenyl-4-pyrone. mp (from methylene chloride/ether)=101°-102.5° C.

Workup

  1. customA flask fitted with a reflux condenser and calcium chloride drying tube
  2. customthe resulting reaction mixture
  3. temperatureis refluxed for 24 hours
  4. temperatureThe mixture is cooled
  5. extractionExtraction with methylene chloride

Sources & evidence

ORD record
ord-a6d02cf2304d41d8a1ee1b33d2e834dc
Source dataset
uspto-grants-1987_12
Patent number
US04714492

Reaction notes

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