3-(6-Benzyloxynaphthalen-2-yl)pentan-3-ol → 6-(1-Ethyl-1-hydroxypropyl)naphthalen-2-ol

HRID 550202Notes

Reaction equation

HRID 550202 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([OH:24])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:13]=[CH:12]2)C1C=CC=CC=1.[H][H]>C(O)C>[CH2:20]([C:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17]2)([OH:24])[CH2:22][CH3:23])[CH3:21]

Participants

4

Reactant 2

HCID 578714103-(6-Benzyloxynaphthalen-2-yl)pentan-3-olHCID 178418361HCID 178418361, compound

Product 1

HCID 578713966-(1-Ethyl-1-hydroxypropyl)naphthalen-2-olYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treat a mixture of 3-(6-benzyloxynaphthalen-2-yl)pentan-3-ol (1.5 g, 4.68 mmol) and 5% PdlAl2CO3 (0.90 g) in ethanol (750 mL) with hydrogen at 60 psi for 8 h at RT. Filter the catalyst from the reaction mixture and concentrate the filtrate to give the title compound as a yellow solid (0.94 g, 87%). MS (ES) m/e 229 (M−1).

Workup

  1. additionTreat
  2. filtrationFilter the catalyst from the reaction mixture
  3. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-1107ca8228d24d54b4d616d75be2ef36
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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