ChemicalBook CAS DataBase List FEMA 3377

FEMA 3377 synthesis

8synthesis methods

Product Name:FEMA 3377
CAS Number:557-48-2
Molecular formula:C9H14O
Molecular Weight:138.21

From natural hexenol

67674-37-7
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Yield:557-48-2 93.2%

Reaction Conditions:

Stage #1:nona-2(Z),6(Z)-dienal diethyl acetal in water at 3 - 8; for 0.166667 h;
Stage #2: with hydrogenchloride in water at 3 - 25; for 2 h;

Steps:

7 6 being C₂H₅)>
(6Z)-1,1-diethoxy-6-nonen-2-yne (7a: two R⁶s being C₂H₅) (23.3 g, 0.111 mol), a P-2Ni catalyst (3.74 g, 0.00197 mol as a nickel compound), and ethanol (71.0 g) were added to a reactor and heated to a temperature of from 45 to 50° C. Then, hydrogen was added and allowed to react for 3 hours. After confirmation of the completion of the reaction, the reaction mixture was cooled to 30° C. and filtered to remove the P-2Ni catalyst. (0171) Then, water (12.8 g) was added to the reaction mixture to wash it. The reaction mixture was phase-separated and the aqueous layer thus obtained was removed. The organic layer was concentrated in a reduced pressure to obtain (2Z,6Z)-1,1-diethoxy-2,6-nonadiene (8: two R⁶being C₂H₅) (19.9 g, 0.0935 mol) in a crude yield of 84.4%. (2Z,6Z)-1,1-Diethoxy-2,6-nonadiene (8: two Rs being C₂H₅) (0172) [Nuclear magnetic resonance spectrum] ¹H-NMR (500 MHz, CDCl₃): δ 0.94 (3H, t, J=7.7 Hz), 1.20 (6H, t, J=7.3 Hz), 2.00-2.06 (2H, m), 2.09-2.13 (2H, m), 2.16-2.21 (2H, m), 3.49 (1H, q, J=7.3 Hz), 3.51 (1H, q, J=7.3 Hz), 3.62 (1H, q, J=7.13 Hz), 3.64 (1H, q, J=7.3 Hz), 5.19 (1H, dd, J=6.9, 1.2 Hz), 5.28-5.34 (1H, m), 5.36-5.41 (1H, m), 5.48 (1H, ddt, J=11.1, 6.9, 1.2 Hz), 5.62 (1H, dtd, 11.1,7.3, 1.2 Hz); ¹³C-NMR (75.6 MHz, CDCl₃): 14.24, 15.26 (2C), 20.50, 26.87, 28,10, 60.46 (2C), 97.65, 127.63, 127.90, 132.36, 134.02 [Mass spectrum] EI-Mass spectrum (70 eV): m/z, 212(M+), 183, 167, 155, 137, 121, 98, 85, 69, 57,41, 29 [Infrared absorption spectrum] (NaCl): vmax 3007, 2974, 2932, 2876, 1658, 1456, 1389, 1317, 1122, 1054, 998, 890, 842, 723