Acetone → HCID 13650577, compound

HRID 1194859Notes

Reaction equation

HRID 1194859 reaction equation
[F:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[CH:11][C:10]4[O:17][CH:18]([CH2:20][OH:21])[CH2:19][C:9]=4[C:8]=3[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.CC(C)=[O:24].S(=O)(=O)(O)O>[O-2].[O-2].[O-2].[Cr+6].O>[F:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[CH:11][C:10]4[O:17][CH:18]([C:20]([OH:24])=[O:21])[CH2:19][C:9]=4[C:8]=3[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 13650575HCID 13650575, compound

Product 1

HCID 13650577HCID 13650577, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

To an ice-cooled mixture of 8.0 g of the 7-fluoro-1,2-dihydro-2-hydroxymethyl-6-oxo-6H-furo[2,3-c]xanthene obtained in Example 27 and 1,000 ml of acetone, a mixture of chromium trioxide (14 g), water (80 ml) and concentrated sulfuric acid (24 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 N,N-dimethylformamide (DMF) gave 8.1 g of 7-fluoro-1,2-dihydro-6-oxo-6H-furo[2,3-c]xanthene-2-carboxylic acid. m.p. 262°-265° C. This compound produced a mass spectrum having a molecular ion peak at m/e 300.

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 N,N-dimethylformamide (DMF)

Sources & evidence

ORD record
ord-4174fa8570ae460cb0ee549570408c2d
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

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