(4-Benzyloxy-naphthalen-1-yloxy)-acetic Acid Ethyl Ester → (4-Hydroxy-naphthalen-1-yloxy)-acetic acid ethyl ester

HRID 1727002Notes

Reaction equation

HRID 1727002 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2]>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 69035941(4-Benzyloxy-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

Product 1

HCID 69037588(4-Hydroxy-naphthalen-1-yloxy)-acetic acid ethyl esterYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.23 g (6.62 mmol) of (4-benzyloxy-naphthalen-1-yloxy)-acetic acid ethyl ester was dissolved in 20 ml of tetrahydrofuran and hydrogenated over 0.5 g of 10% of palladium on charcoal as catalyst at ambient temperature and atmospheric pressure. Filtering off the catalyst and evaporating the solvent yielded 1.2 g of the title compound as light brown solid.

Workup

  1. filtrationFiltering off the catalyst
  2. customevaporating the solvent

Sources & evidence

ORD record
ord-c012bd1cc1394387a1f392d36b6dc0eb
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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