Abstract
A three-step synthesis of 2-nonen-4-olide starting from heptanal is reported. (E)-3-Nonenoic acid, prepared by Knoevenagel condensation of malonic acid and heptanal, was oxidised by performic acid, a process accompanied by lactonisation, to give 3-hydroxynonan-4-olide in 85% yield. This lactone when reacted with MsCl in the presence of Et3N gave, by elimination, 2-nonen-4-olide in 88% yield. The overall yield was 75%. The odour of the product was evaluated by GC-olfactory analysis and sniffing blotter confirming an oily, coconut-like, and rancid odour.
References
1.
Christlbauer M.
, and
Schieberle P.
, J. Agric. Food Chem. , 2009 , 57 , 9114 .
2.
Gullén M.D.
,
Goicoechea E.
,
Palencia G.
, and
Cosmes N.
, J. Agric. Food Chem. , 2008 , 56 , 2028 .
3.
Lin L.Y.
,
Peng C.H.
,
Wang H.E.
,
Wu T.H.
,
Chen C.C.
,
Yu T.H.
,
Wu C.M.
, and
Peng R.Y.
, Flavour Fragr. J. , 2007 , 22 , 274 .
4.
Beaulieu J.C.
, and
Lea J.M.
, J. Agric. Food Chem. , 2006 , 54 , 7789 .
5.
Sanches-Silva A.
,
Lopez-Hernández J.
, and
Paseiro-Losada P.
, J. Chromatogr. A , 2005 , 1064 , 239 .
6.
Paleari M.A.
,
Moretti V.M.
,
Bersani C.
,
Beretta G.
, and
Mentasti T.
, Meat Sci. , 2004 , 67 , 549 .
7.
Lisárraga-Guerra R.
,
Guth H.
, and
López M.G.
, J. Agric. Food Chem. , 1997 , 45 , 1329 .
8.
Wagner R.
, and
Grosch W.
, Lebensm.-Wiss. Technol. , 1997 , 30 , 164 .
9.
Shu N.
, and
Shen H.
, Flavour Fragr. J. , 2009 , 24 , 1 .
10.
Weeks W.W.
,
Chaplin J.F.
, and
Campbell C.R.
, J. Agric. Food Chem. , 1989 , 37 , 1038 .
11.
Smith R.L.
,
Cohen S.M.
,
Doull J.
,
Feron V.J.
,
Goodman J.I.
,
Marnett L.J.
,
Portoghese P.S.
,
Waddell W.J.
,
Wagner B.M.
, and
Adams T.B.
, Food Technol. , 2005 , 59 , 24 .
12.
Strand D.
, and
Rein T.
, Org. Lett. , 2005 , 7 , 199 .
13.
Cheung A.K.
,
Murelli R.
, and
Snapper M.L.
, J. Org. Chem. , 2004 , 69 , 5712 .
14.
Marshall J.A.
,
Piettre A.
,
Paige M.A.
, and
Valeriote F.
, J. Org. Chem. , 2003 , 68 , 1780 .
15.
Schmidt B.
, and
Geißler D.
, Eur. J. Org. Chem. , 2011 , 7140 .
16.
Fürstner A.
,
Thiel O.R.
,
Ackermann L.
,
Schanz H-J.
, and
Nolan S.P.
, J. Org. Chem. , 2000 , 65 , 2204 .
17.
Browne D.M.
,
Niyomura O.
, and
Wirth T.
, Org. Lett. , 2007 , 9 , 3169 .
18.
Chen Y.-Z.
,
Wu L.-Z.
,
Peng M.-L.
,
Zhang D.
,
Zhang L.-P.
, and
Tung C.-H.
, Tetrahedron , 2006 , 62 , 10688 .
19.
Bonete P.
, and
Nájera C.
, Tetrahedron , 1995 , 51 , 2763 .
20.
Ragoussis N.
, Tetrahedron Lett. , 1987 , 28 , 93 .
21.
Braukmüller S.
, and
Brückner R.
, Eur. J. Org. Chem. , 2006 , 2110 .
22.
Xiao Y.
,
Tian H.-Y.
,
Zhang S.-S.
, and
Sun B.-G.
, Riyonghuaxuegongye (in Chinese), 2010 , 40 , 194 .