Reaction #1973956

Reaction equation

methyl 6-bromo-2-naphthoate

THF

lithium hydroxide hydrate

→

title compound

6-bromo-2-naphthoic acid

Solvents

water

Conditions

Workup

1. 1
   ConcentrationConcentrated under vacuum
2. 2
   workup.ADDITIONdiluted with water
3. 3
   Temperaturecooled to 0° C
4. 4
   FiltrationSolids were collected by filtration
5. 5
   workup.DISSOLUTIONdissolved in toluene-EtOAc (ca. 2 L)
6. 6
   Washwashed with brine
7. 7
   DryingDried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated under vacuum
10. 10
    OtherBrown solid was triturated with ether
11. 11
    Filtrationcollected by filtration
12. 12
    Otherdried under vacuum

Procedure

A solution of methyl 6-bromo-2-naphthoate (7.70 g, 29.0 mmol) in 2:1 THF:water (150 mL) was treated with lithium hydroxide hydrate (2.44 g, 58.1 mmol) followed by stirring at room temperature for 48 h. Concentrated under vacuum, diluted with water and cooled to 0° C. Acidified to pH3 with 4N HCl. Solids were collected by filtration, dissolved in toluene-EtOAc (ca. 2 L) and washed with brine. Dried over Na2SO4, filtered and concentrated under vacuum. Brown solid was triturated with ether, collected by filtration, and dried under vacuum to give the title compound as a nearly white solid (5.07 g, 70%).

Source