7-(Benzyloxy)-2-naphthoic acid → 7-Hydroxy-2-naphthoic acid

HRID 890956Notes

Reaction equation

HRID 890956 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 222434307-(Benzyloxy)-2-naphthoic acid

Product 1

HCID 145125257-Hydroxy-2-naphthoic acidYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 7-benzyloxy-2-naphthoic acid (208 mg, 0.75 mmol) and 10% palladium on carbon (208 mg) in 1,4-cyclohaxadiene (1 mL) and ethanol (2 mL) is heated at 60° C. for 24 hours. The reaction is allowed to cool and filtered through a plug of AG50W×2 resin (H+ form). The plug is washed with methanol and the washes are evaporated to dryness to give 7-hydroxy-2-naphthoic acid as a tan solid (87 mg, 62%). 1H NMR (400 MHz, CD3OD) δ 8.4, 7.8, 7.2.

Workup

  1. temperatureto cool
  2. filtrationfiltered through a plug of AG50W×2 resin (H+ form)
  3. washThe plug is washed with methanol
  4. customthe washes are evaporated to dryness

Sources & evidence

ORD record
ord-4c1c46dd12af480584a19b33393d2d6d
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Reaction notes

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