Sodium Hydroxide → 7-Bromo-3-methoxy-2-naphthoic acid

HRID 1773546Notes

Reaction equation

HRID 1773546 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[C:16]([O:17][CH3:18])=[CH:15][C:14]2[C:9](=[CH:10][C:11]([Br:19])=[CH:12][CH:13]=2)[CH:8]=1)=[O:6]>O.C(O)C>[Br:19][C:11]1[CH:10]=[C:9]2[C:14]([CH:15]=[C:16]([O:17][CH3:18])[C:7]([C:5]([OH:6])=[O:4])=[CH:8]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14528105Methyl 7-bromo-3-methoxy-2-naphthoate

Product 1

HCID 145281067-Bromo-3-methoxy-2-naphthoic acidYield 94.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (1.6 g, 40 mmol) in water (30 mL) was added to a solution of 7-bromo-3-methoxy-naphthalene-2-carboxylic acid methyl ester (5.9 g, 20 mmol) in ethanol (100 mL) and the resulting mixture was heated at reflux for 2 hours. The reaction mixture was then cooled and concentrated under reduced pressure. The residue was acidified until pH 3 ca. by addition of an aqueous solution of hydrochloric acid. The resulting mixture was extracted twice with dichloromethane and the combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 5.329 g of 7-bromo-3-methoxy-naphthalene-2-carboxylic acid as a cream colored solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction mixture was then cooled
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was acidified until pH 3 ca. by addition of an aqueous solution of hydrochloric acid
  6. extractionThe resulting mixture was extracted twice with dichloromethane
  7. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5087693cfd90487f9d3eaf241382ef6b
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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