Ethyl 2-(3-(benzyloxy)naphthalen-1-yl)acetate → Ethyl 2-(3-hydroxynaphthalen-1-yl)acetate

HRID 900148Notes

Reaction equation

HRID 900148 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([O:16]CC2C=CC=CC=2)[CH:7]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([OH:16])[CH:7]=1)[CH3:2]

Participants

4

Reactant 1

HCID 44479435Ethyl 2-(3-(benzyloxy)naphthalen-1-yl)acetate

Product 1

HCID 68902456Ethyl 2-(3-hydroxynaphthalen-1-yl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(3-Benzyloxy-naphthalen-1-yl)-acetic acid ethyl ester (2.43 g, 7.58 mmol) is dissolved in MeOH (50 ml). Palladium on charcoal (807 mg) is added, and the reaction mixture is stirred at RT under an atmosphere of hydrogen (1 atm) for 14 h. The reaction mixture is filtered. Concentration yields the pure title compound. 1H NMR (DMSO, 400 MHz) δ 1.18 (t, J=7.2 Hz, 3H), 4.05 (s, 2H), 4.10 (q, J=7.2 Hz, 2H), 7.04 (d, J=1.8 Hz, 1H), 7.06 (d, J=1.8, 1H), 7.30 (t, J=7.8, 1H), 7.40 (t, J=7.8, 1H), 7.70 (d, J=7.8, 1H), 7.80 (d, J=7.8 Hz, 1H); ES-MS: 230 [M+H]+.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationConcentration

Sources & evidence

ORD record
ord-b2d04c1d3a5242cabd98d220c4e9b997
Source dataset
uspto-grants-2008_04
Patent number
US07358253B2

Reaction notes

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