Boron tribromide → 1-Hydroxy-4-naphthoic acid

HRID 1866170Notes

Reaction equation

HRID 1866170 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 7653804-Methoxynaphthalene-1-carboxylic acid

Product 1

HCID 3442911-Hydroxy-4-naphthoic acidYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, 4-methoxy-1-naphthoic acid (4.33 g) in dichloromethane (45 ml) was added boron tribromide (1M in dichloromethane, 63 ml) dropwise at 0° C., and the mixture was stirred at the same temperature for 2 hours. The resulting mixture was poured into ice-cold water and the precipitate was collected by filtration. The filter cake was added to the mixture of water and ethyl acetate, and then adjusted to pH 9 with 1N sodium hydroxide. After separation, the organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to afford 4-hydroxy-1-naphthoic acid (2.19 g) as a colorless powder.

Workup

  1. additionThe resulting mixture was poured into ice-cold water
  2. filtrationthe precipitate was collected by filtration
  3. additionThe filter cake was added to the mixture of water and ethyl acetate
  4. customAfter separation
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-a09a54da681d44dbb0bebda739fe263b
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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