Acetone → HCID 13650570, compound

HRID 543411Notes

Reaction equation

HRID 543411 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-12ab645f8a404091ac7b17c70fc58bda
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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