Reacción #2045060

ord-3b4904dd81ec4c0a9eaf69bcc67ee669

Ecuación de reacción

COC(=O)C(C)c1ccc2cc(OC(=O)COCc3ccccc3)ccc2c1
2-[6-(2-Benzyloxyacetoxy)naphthalen-2-yl]propionic acid methyl ester
COC(=O)C(C)c1ccc2cc(OC(=O)CO)ccc2c1
100
Rendimiento 78.9%
COC(=O)C(C)c1ccc2cc(OC(=O)CO)ccc2c1
2-[6-(2-Hydroxyacetoxy)naphthalen-2-yl]propionic acid methyl ester
Rendimiento 78.9%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe catalyst was removed by filtration and ethyl acetate
  2. 2
    workup.DISTILLATIONdistilled off under vacuum
  3. 3
    workup.ADDITIONHexane was added
  4. 4
    Otroto precipitate
  5. 5
    Filtraciónfiltered

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08409559B2uspto-grants-2013_04