TCI B6389, 3-(benzyloxy)propanal (CAS 19790-60-4), is a three-carbon aldehyde whose terminal hydroxyl is masked as a benzyl ether, giving far better stability than the free 3-hydroxypropanal. It is widely used in Wittig and Horner-Wadsworth-Emmons olefinations, aldol chemistry, reductive aminations, and organometallic additions. After the carbon framework is assembled, the benzyl group can be removed cleanly by hydrogenolysis to reveal the primary alcohol, a strategy common in natural product synthesis. Supplied as a 1 g pack, it is air-sensitive and best stored cold under an inert atmosphere, protected from light.
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- (2002). SYNTHESIS OF (−)-(E,S)-3-(BENZYLOXY)-1-BUTENYL PHENYL SULFONE VIA A HORNER-WADSWORTH-EMMONS REACTION OF (−)-(S)-2-(BENZYLOXY)PROPANAL. Organic Syntheses doi:10.15227/orgsyn.078.0177
- VARELIS et al. (1996). ChemInform Abstract: Preparation of Optically Active (S)‐2‐(Benzyloxy)propanal.. ChemInform doi:10.1002/chin.199607096
- Varelis et al. (1995). Preparation of Optically Active (S)-2-(Benzyloxy)propanal. Australian Journal of Chemistry doi:10.1071/ch9951775
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