Acetone → HCID 13650570, compound

HRID 1194858Notes

Reaction equation

HRID 1194858 reaction equation
[OH:1][CH2:2][CH:3]1[O:19][C:18]2[C:5](=[CH:6][C:7]3[C:8](=[O:21])[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[O:15][C:16]=3[C:17]=2[CH3:20])[CH2:4]1.CC(C)=[O:24].S(=O)(=O)(O)O>[O-2].[O-2].[O-2].[Cr+6].O>[CH3:20][C:17]1[C:16]2[O:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8](=[O:21])[C:7]=2[CH:6]=[C:5]2[CH2:4][CH:3]([C:2]([OH:24])=[O:1])[O:19][C:18]=12

Participants

6

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 13650569HCID 13650569, compound

Product 1

HCID 13650570HCID 13650570, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

To an ice-cooled mixture of 16.1 of the 2,3-dihydro-2-hydroxymethyl-11-methyl-5-oxo-5H-furo[3,2-b]xanthene obtained in Example 25 and 3,000 ml of acetone, a mixture of chromium trioxide (57 g), water (280 ml) and concentrated sulfuric acid (84 g) was added dropwise under agitation. The resulting mixture was left to stand overnight and filtered. The filtrate was evaporated to dryness under vacuum. After addition of water, the solid crystal was recovered by filtration, washed with water and dried. Recrystallization from a mixed solvent of methanol and dichloromethane gave 11.1 g of 2,3-dihydro-11-methyl-5-oxo-5H-furo[3,2-b]xanthene-2-carboxylic acid. m.p. 297°-299° C. This compound produced a mass spectrum having a molecular ion peak at m/e 296.

Workup

  1. additionwas added dropwise under agitation
  2. waitThe resulting mixture was left
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness under vacuum
  5. additionAfter addition of water
  6. filtrationthe solid crystal was recovered by filtration
  7. washwashed with water
  8. customdried
  9. customRecrystallization from a mixed solvent of methanol and dichloromethane

Sources & evidence

ORD record
ord-d4905e34fdf64ead97294650bc18f082
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

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