2-[p-(Benzyloxy)phenoxy]propionaldehyde → 2-(4-Hydroxyphenoxy)propanal

HRID 249203Notes

Reaction equation

HRID 249203 reaction equation
C([O:8][C:9]1[CH:19]=[CH:18][C:12]([O:13][CH:14]([CH3:17])[CH:15]=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH3:17])[CH:15]=[O:16])=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 189627142-[p-(Benzyloxy)phenoxy]propionaldehyde

Product 1

HCID 189627082-(4-Hydroxyphenoxy)propanalYield 36.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-[p-(benzyloxy)phenoxy]propionaldehyde (34.6 g, 0.135 mol) and 5% Pd on carbon (2.0 g) in ethanol (250 mL) is placed on a Parr hydrogenerator. Over 5 hours, the pressure drops from 37 psi to 28 psi. The reaction mixture is then filtered through celite and concentrated in vacuo to obtain a dark yellow syrup. Flash chromatography of the syrup using silica gel and eluting with methylene chloride followed by 1% to 10% ethyl acetate in methylene chloride gives the title product as a dark yellow syrup (8.2 g) which is identified by 1H NMR spectral analysis.

Workup

  1. filtrationThe reaction mixture is then filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customto obtain a dark yellow syrup
  4. washeluting with methylene chloride

Sources & evidence

ORD record
ord-304c5e9c0b1c4e70b7f6b8167b4c6617
Source dataset
uspto-grants-1993_05
Patent number
US05213606

Reaction notes

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