Rheosmin (“Raspberry Ketone”) and Zingerone, and Their Preparation by Crossed Aldol-Catalytic Hydrogenation Sequences

@article{Smith1996RheosminK,
  title={Rheosmin (“Raspberry Ketone”) and Zingerone, and Their Preparation by Crossed Aldol-Catalytic Hydrogenation Sequences},
  author={L. R. Smith},
  journal={The Chemical Educator},
  year={1996},
  volume={1},
  pages={1-18}
}
  • L. R. Smith
  • Published 1996
  • Chemistry
  • The Chemical Educator
  • Preparations of the two closely-related natural products rheosmin (“raspberry ketone”, 4-(4′-hydroxyphenyl)-2-butanone) and zingerone (4-(4′-hydroxy-3′-methoxyphenyl)-2-butanone), are well-suited for the introductory organic laboratory. The crossed-aldol condensation of 4-hydroxybenzaldehyde with acetone gives an adduct (4-(4′-hydroxyphenyl)-3-buten-2-one), which is hydrogenated cleanly over rhodium on alumina to form rheosmin. Condensation of vanillin with acetone gives 4-(4′-hydroxy-3… CONTINUE READING
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