Phosphate → HCID 13660407, compound

HRID 414627Notes

Reaction equation

HRID 414627 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][C:13](=[O:15])[CH3:14])=[C:7]([O:16][CH3:17])[C:6]([O:18][CH3:19])=[C:5]2[O:20]C(=O)C.P([O-])([O-])([O-])=O.P([O-])([O-])(O)=O.[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][C:13](=[O:15])[CH3:14])=[C:7]([O:16][CH3:17])[C:6]([O:18][CH3:19])=[C:5]2[OH:20]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 24203Sodium Phosphate, DibasicHCID 56237Lonapalene

Product 1

HCID 13660407HCID 13660407, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ten grams of 6-chloro-2,3-dimethoxy-1,4-diacetyloxynaphthalene, 150 ml of 0.05M, pH 8, phosphate buffer solution and 150 ml of acetonitrile were heated at 80° C. for 10 days. The reaction was monitored by TLC. Additional disodium hydrogen phosphate was added to maintain the reaction mixture at pH 8. The reaction mixture was cooled and solvent evaporated and the resultant residue was extracted with ethyl acetate (3X), washed with 1M HCl (2X) and brine (2X). The solution was dried over sodium sulfate, filtered and evaporated. The residue which is an isomeric mixture was recrystallized from petroleum ether and gave 2.0 gm 6-chloro-2,3-dimethoxy-1-acetyloxy-4-hydroxynaphthalene, m.p. 155°-6° C.

Workup

  1. temperatureto maintain the reaction mixture at pH 8
  2. temperatureThe reaction mixture was cooled
  3. customsolvent evaporated
  4. extractionthe resultant residue was extracted with ethyl acetate (3X)
  5. washwashed with 1M HCl (2X) and brine (2X)
  6. dry with materialThe solution was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-979cd786392b4bc9ba2da01a477fbf1b
Source dataset
uspto-grants-1988_12
Patent number
US04792556

Reaction notes

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