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

HRID 1976943Notes

Reaction equation

HRID 1976943 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 Büchner 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 Büchner 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-8f24f3fb66314952bfdebec4124ae7ea
Source dataset
uspto-grants-2001_05
Patent number
US06229055B1

Reaction notes

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