Efficient aldol condensation in aqueous biphasic system under microfluidic conditions

Tetrahedron Letters

Volumn 49, Issue 12, 2008, Pages 2010-2012

  Tanaka, Katsunori ^a   Motomatsu, Shinya ^a,b   Koyama, Koichi ^b   Fukase, Koichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b Kishida Chemical Co Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ACETONE ENOLATE; ALDEHYDE; PROTON; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; HEAT TRANSFER; LIQUID; LIQUID CULTURE; MICROFLUIDIC ANALYSIS;

EID: 39249084577     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.057     Document Type: Article

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22. 2O and ∼20 for α-proton of carbonyls).
23. In order to compare the microfluidic and the batch conditions, the same concentrations of the aldehydes (in acetone) and the aqueous NaOH solution were used for the batch reaction: A 5.5 M solution of the aldehyde (1.5 mol scale) in acetone was added to the premixed biphasic solution of acetone and 2.5 M NaOH (2.7:1) at 8.5 °C over 1.5-3 h.
24. 4, filtered, and concentrated in vacuo to give the crude product. The residue was purified by distillation under reduced pressure (50-70 °C/20 mm Hg) to afford 7 (17 g, 95%). The spectrum data were in good agreement to those reported in Ref. 10. The conditions established herein can be readily applicable to the scale-up synthesis simply by preparing the stock solutions of substrate and reagents and pumping them continuously into the micromixing system.
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26. Geranyl aldehyde 5 was obtained by manganese dioxide oxidation of geraniol. Crude 5 was directly used for the aldol reaction with acetone.