Practical synthesis of 3-methylnonane-2,4-dione, an intense strawlike and fruity flavored compound.
A practical synthesis of 3-methylnonane-2,4-dione, which is an intense strawlike and fruity flavored compound, has been performed by the aldol condensation of n-hexanal and methyl ethyl ketone, followed by oxidation using sodium hypochlorite in the presence of 4-benzoyloxy-2,2,6,6-tetramethylpiperidine-N-oxide in an overall yield of 59%. The purification of 3-methylnonane-2,4-dione with high purity was performed via copper complexes.
Kato
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Y
Technical Engineering Department, Fine Chemical Division, Takasago International Corporation, 1-5-1 Nishiyawata, Hiratsuka, Kanagawa 254-0073, Japan.
Yuasa
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Y
D000447:Aldehydes / Q000737:chemistry; D000473:Alkanes / Q000138:chemical synthesis*; D002074:Butanones / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D005421:Flavoring Agents / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis*; D009812:Odorants; D010084:Oxidation-Reduction; D012973:Sodium Hypochlorite / Q000737:chemistry; D013024:Soybean Oil / Q000737:chemistry*; D013649:Taste
C439225:3-methylnonane-2,4-dione; D000447:Aldehydes; D000473:Alkanes; D002074:Butanones; D005421:Flavoring Agents; D007659:Ketones; C005222:methylethyl ketone; D003300:Copper; D013024:Soybean Oil; C116609:3-hydroxybutanal; C010463:n-hexanal; D012973:Sodium Hypochlorite