Reaction #2045060

Reaction equation

2-[6-(2-Benzyloxyacetoxy)naphthalen-2-yl]propionic acid methyl ester

→

100

Yield 78.9%

2-[6-(2-Hydroxyacetoxy)naphthalen-2-yl]propionic acid methyl ester

Yield 78.9%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration and ethyl acetate
2. 2
   workup.DISTILLATIONdistilled off under vacuum
3. 3
   workup.ADDITIONHexane was added
4. 4
   Otherto precipitate
5. 5
   Filtrationfiltered

Procedure

2-[6-(2-Benzyloxyacetoxy)naphthalen-2-yl]propionic acid methyl ester 99 (5 g, 13.22 mmol) was dissolved in ethyl acetate (50 ml) in a pressure vessel, palladium on carbon (5%, 3 g) added and the mixture stirred under a hydrogen atm. (3.5 Kg) for 4 hrs. The catalyst was removed by filtration and ethyl acetate distilled off under vacuum. Hexane was added to precipitate and filtered to give pure 100 (3 g, 78.9%) as off-white powder. M.p: 49.5-52° C.

Source