ChemicalBook CAS DataBase List 4-DODECYLOXYBENZONITRILE

4-DODECYLOXYBENZONITRILE synthesis

3synthesis methods

Product Name:4-DODECYLOXYBENZONITRILE
CAS Number:29147-92-0
Molecular formula:C19H29NO
Molecular Weight:287.44

767-00-0 Synthesis

767-00-0
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143-15-7 Synthesis

143-15-7
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29147-92-0
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Yield:29147-92-0 93%

Reaction Conditions:

with potassium carbonate in butanone; for 24 h;Reflux;

Steps:

4.5.1. 4-(Dodecyloxy)benzonitrile (3)

Firstly, 15.00 g (126.0 mmol) of 4-hydroxybenzonitrile (1), 42.30 mL (176.0 mmol) of 1-bromododecane, 52.20 g (378.0 mmol) of K₂CO₃, and 350 mL of butanone were placed into a 500 mL round-bottomed flask equipped with a condenser. The mixture was then refluxed and stirred for 24 h. After this period, the suspension was filtered and washed with hot butanone. The solvent was removed by rotary evaporation and the solid obtained was recrystallized on ethanol, affording 33.60 g of a white crystals (93%), mp 41.5-44.0 °C (lit. 42-43 °C).²⁵ IR (KBr, cm^-1): ν_max: 2916, 2850, 2218 (CN), 1608, 1509, 1302, 1256, 1172, 833, 547. ¹H NMR (CDCl₃), δ, ppm: 7.55 (d, J=8.9 Hz, 2H, Ar-H), 6.92 (d, J=8.9 Hz, 2H, Ar-H), 3.98 (t, J=6.6 Hz, 2H, -OCH₂-), 1.78 (qt, J=6.6 Hz, 2H, -OCH₂CH₂-), 1.44 (m, 2H, -CH₂-), 1.22-1.33 (br, 16H, -CH₂-), 0.87 (t, J=6.7 Hz, 3H, -CH₃). ¹³C NMR (CDCl₃), δ, ppm: 162.7, 134.2, 119.5, 115.4, 103.8, 68.6, 32.2, 29.9, 29.9, 14.9.

References:

Gallardo, Hugo;Ferreira, Marli;Vieira, André A.;Westphal, Eduard;Molin, Fernando;Eccher, Juliana;Bechtold, Ivan H. [Tetrahedron,2011,vol. 67,# 49,p. 9491 - 9499] Location in patent:experimental part

112-53-8 Synthesis