Sulfuric Acid → HCID 14075263, compound

HRID 2107891Notes

Reaction equation

HRID 2107891 reaction equation
OS(O)(=O)=O.[CH:6]([O:11][CH3:12])([O:9]C)OC.[Cl:13][C:14]1[CH:30]=[CH:29][C:17]([C:18]([C:20]2C(=O)[O:22][C:23]([CH3:27])=[CH:24][C:25]=2[OH:26])=O)=[CH:16][CH:15]=1.C(OC)=O>CO>[CH3:12][O:11][C:6]([C:20]1[C:25](=[O:26])[CH:24]=[C:23]([CH3:27])[O:22][C:18]=1[C:17]1[CH:16]=[CH:15][C:14]([Cl:13])=[CH:30][CH:29]=1)=[O:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7865Methyl formateHCID 9005Trimethyl orthoformateHCID 1359690263-(4'-Chlorobenzoyl)-4-hydroxy-6-methyl-2-pyrone

Product 1

HCID 14075263HCID 14075263, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5000 ml 3-neck flask is fitted with a N2 inlet, magnetic stirring bar, thermometer and a Dean-Stark trap with condenser. 2300 mls of dry methanol is added to the flask along with 244 gms of 96% H2SO4 and 352 gms of trimethyl orthoformate. 173 gms of 3-(4'-chlorobenzoyl)-4-hydroxy-6-methyl-2-pyrone is added and the reaction mixture is gently brought to reflux. The most volatile by-product of the reaction (methyl formate) is condensed and collected in the Dean-Stark trap. After 281/2 hours of reflux the reaction mixture is cooled to room temperature and poured into 6000 mls of brine. The resulting suspension is extracted with methylene chloride (6×250 mls). Evaporation of the solvent yields 153 gms of 3-methoxycarbonyl-6-methyl-2-(4'-chlorophenyl)-4-pyrone. mp (methylene chloride/ether)=131-2.

Workup

  1. customA 5000 ml 3-neck flask is fitted with a N2 inlet, magnetic stirring bar
  2. temperatureto reflux
  3. customcondensed
  4. customcollected in the Dean-Stark trap
  5. temperatureAfter 281/2 hours of reflux the reaction mixture
  6. additionpoured into 6000 mls of brine
  7. extractionThe resulting suspension is extracted with methylene chloride (6×250 mls)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8c60ae8e33b348ea87711e421021944c
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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