2-[p-(Benzyloxy)phenoxy]propionaldehyde → 2-(4-Hydroxyphenoxy)propanal
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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.