4-Benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester → (4-Hydroxy-naphthalen-2-yl)-acetic acid methyl ester

HRID 238606Notes

Reaction equation

HRID 238606 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10](Cl)[CH:11]=2)[CH:6]=1.COC(C1C=C(OCC2C=CC=CC=2)C2C(=CC=C(F)C=2)C=1)=O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 593265854-Benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl esterHCID 67304221(4-Benzyloxy-6-chloro-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326576(4-Hydroxy-naphthalen-2-yl)-acetic acid methyl esterYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (4-benzyloxy-6-chloro-naphthalen-2-yl)-acetic acid methyl ester (340 mg, 1.0 mmol, prepared using a method analogous to the one described above for the preparation of 4-benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester, 1st-7th step for example 1-1) in methanol was added 10% palladium on carbon (10 mg). The resulting mixture was vigorously stirred at room temperature overnight under a hydrogen atmosphere (balloon) and then filtered. The filtrate was concentrated in vacuo to give (4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (200 mg, 92.6%) as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ad122fefb84f4a5e917e8695be6bc7f3
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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