1-Naphthaldehyde → 2,7-Difluoro-6-hydroxy-1-(1-naphthyl)xanthene-3-one

HRID 1275940Notes

Reaction equation

HRID 1275940 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].[C:10]1([CH:20]=O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1>CS(O)(=O)=O>[F:1][C:2]1[C:3](=[O:9])[CH:4]=[C:5]2[C:7](=[CH:8][C:7]3[C:5]([O:6]2)=[CH:4][C:3]([OH:9])=[C:2]([F:1])[CH:8]=3)[C:20]=1[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 61951-NaphthaldehydeHCID 105586404-Fluoro-1,3-dihydroxybenzene2×

Product 1

HCID 219995082,7-Difluoro-6-hydroxy-1-(1-naphthyl)xanthene-3-one

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

Two equivalents of 4-fluororesorcinol (Compound 15) are condensed with one equivalent of naphthalene-1-carboxaldehyde in warm methanesulfonic acid. When the reaction is judged complete by TLC analysis, the intermediate product is precipitated from the reaction solution by the addition of an excess of water. The crude solid is collected on a Buichner funnel, and dried in vacuo. The intermediate is then dissolved in chloroform and treated with an excess of chloramine-T. When the oxidation reaction is complete, as judged by TLC, the volatiles are removed in vacuo and the crude product is purified using flash chromatography to give Compound 57.

Workup

  1. customthe intermediate product is precipitated from the reaction solution by the addition of an excess of water
  2. customThe crude solid is collected on a Buichner funnel
  3. customdried in vacuo
  4. dissolutionThe intermediate is then dissolved in chloroform
  5. additiontreated with an excess of chloramine-T
  6. customWhen the oxidation reaction
  7. customthe volatiles are removed in vacuo
  8. customthe crude product is purified

Sources & evidence

ORD record
ord-816f9ebc5a0445b9a4c38d48ad66e0aa
Source dataset
uspto-grants-2000_12
Patent number
US06162931

Reaction notes

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