Sodium Hydroxide → HCID 21696412, compound

HRID 378754Notes

Reaction equation

HRID 378754 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[C:10]([O:21]C(=O)C)=[CH:9][C:8]=2[C:25]([O:27]C)=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[C:10]([OH:21])=[CH:9][C:8]=2[C:25]([OH:27])=[O:26])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18369992HCID 18369992, compound

Product 1

HCID 21696412HCID 21696412, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Phenyl-2-methoxycarbonyl-4-acetoxy-6,7-dimethoxynaphthalene (66.4 grams) from Step 3, 500 mL of a 10 weight percent aqueous sodium hydroxide solution and 50 mL of methanol were added to a reaction flask and heated to reflux for 3 hours and then cooled to room temperature. The reaction mixture was poured onto an aqueous solution of 4N hydrochloric acid/ice mixture (˜400 mL). A white precipitate formed and was collected by vacuum filtration, washed with water and was air-dried. Recrystallization from ethanol (95 weight percent) gave 57 grams of 1-phenyl-4-hydroxy-6,7-dimethoxy-2-naphthoic acid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customA white precipitate formed
  4. filtrationwas collected by vacuum filtration
  5. washwashed with water
  6. customwas air-dried
  7. customRecrystallization from ethanol (95 weight percent)

Sources & evidence

ORD record
ord-569aa3c54bb04ab58ccf738ad83df48a
Source dataset
uspto-grants-2001_10
Patent number
US06296785B1

Reaction notes

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