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

HRID 1957878Notes

Reaction equation

HRID 1957878 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][C:17](=[O:27])[CH2:18][O:19]CC3C=CC=CC=3)[CH:12]=2)[CH:7]=1)[CH3:5]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][C:17](=[O:27])[CH2:18][OH:19])[CH:12]=2)[CH:7]=1)[CH3:5]

Participants

4

Reactant 1

HCID 592539682-[6-(2-Benzyloxyacetoxy)naphthalen-2-yl]propionic acid methyl ester

Product 1

HCID 592539672-[6-(2-Hydroxyacetoxy)naphthalen-2-yl]propionic acid methyl esterYield 78.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. customThe catalyst was removed by filtration and ethyl acetate
  2. distillationdistilled off under vacuum
  3. additionHexane was added
  4. customto precipitate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-3b4904dd81ec4c0a9eaf69bcc67ee669
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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