Sodium Hydroxide → HCID 17842552, compound

HRID 546441Notes

Reaction equation

HRID 546441 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14]C)=[O:13])[CH:6]=[C:5]2[OH:16].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[C:5]2[OH:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5745058HCID 5745058, compound

Product 1

HCID 17842552HCID 17842552, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Chloro-4-hydroxy-2-methoxycarbonylnaphthalene (J. Chem. Research (S), 1995, p. 638) (473 mg) was dissolved in ethanol (10 ml), and a 1N aqueous solution (4.0 ml) of sodium hydroxide was added to stir the mixture for 24 hours at room temperature. Thereafter, the reaction mixture was stirred for 1 hour at 60° C. and 6 hours at 70° C., and the solvent was distilled off under reduced pressure. An 1N aqueous solution of hydrochloric acid and ethyl acetate were added to separate an organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (442 mg) as a pale yellow solid.

Workup

  1. stirringThereafter, the reaction mixture was stirred for 1 hour at 60° C. and 6 hours at 70° C.
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionAn 1N aqueous solution of hydrochloric acid and ethyl acetate were added
  4. customto separate an organic layer
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0f7724904132452db2b540312b7e8666
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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