Detail of "36255-44-4"

Reference

Perfume compositions

Perfume compositions. (Naarden International N. V., Neth.). Neth. Appl. NL 7608333 31 Jan 1978, 11 pp. (Dutch). (Netherlands). CODEN: NAXXAN. CLASS: IC: A61K007-46. APPLICATION: NL 76-8333 27 Jul 1976. DOCUMENT TYPE: Patent CA Section: 62 (Essential Oils and Cosmetics) Section cross-reference(s): 23 4-Heptynal [21891-36-1], an intermediate in manuf. of the perfume and flavoring components cis-4-heptenal [6728-31-0], 2,6-nonadienal [26370-28-5], and 2,6-nonadienol [7786-44-9] and of the new perfume component 2,6-nonadienenitrile [67019-89-0], is readily prepd. from 1-butyne [107-00-6] and acrolein [107-02-8]. Thus, 240 g MeOH was cooled to 5°, 202 g HBr was passed in over 1.5 h, and 140 g acrolein was added over a further 1.5 h and stirred. The lower layer contained a-bromopropionaldehyde di-Me acetal (I) [36255-44-4]. To 0.75 L NH3 in a sep. vessel were added successively 0.1 g Fe(NO3)3, 3.5 g Li in small portions, 0.1 g Ph3CH, 34 g 1-butyne to form the Li butynylide, and 0.5 mol I with stirring. After evapn. of the NH3 and addn. of 105 g hexane, 25 g MeOH, and 105 mL water, the hexane layer was isolated, evapd., and distd. under vacuum to yield 4-heptynal di-Me acetal [66840-10-6], which was cleaved to 4-heptynal. 4-Heptynal was hydrogenated over Lindlar catalyst to cis-4-heptynal, and 15 g of this compd. was added to a refluxing mixt. of 12 g cyanoacetic acid [372-09-8] and a small amt. of b-alanine in 150 mL C6H6. The reaction mixt. was evapd. and the residue dissolved in 300 mL pyridine and refluxed for 1.5 h in the presence of Cu powder. The pyridine was distd. off, and the residue was distd. under vacuum to yield 7 g 2,6-nonadienenitrile. This compd. had a cucumber-like odor with reseda notes.