ChemicalBook CAS DataBase List 2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE

2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE synthesis

10synthesis methods

Product Name:2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE
CAS Number:33143-29-2
Molecular formula:C12H11NO
Molecular Weight:185.22

4-[(1,1-DIMETHYLPROP-2-YNYL)OXY]BENZONITRILE

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33143-29-2
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Yield: 100%

Reaction Conditions:

in ethylene glycol at 210 - 215; for 24 h;

Steps:

4.5. 6-Cyano-2,2-dimethylchromene 16 Method B
Phenyl propargyl ether 18 (1.0 g, 5.40 mmol) was dissolved in ethylene glycol (5 mL/g of the propargyl ether) and thereaction mixture heated to 210e215 C for 24 h. The mixture wasallowed to cool to room temperature and water added. The mixturewas extracted with Et2O (2 25 mL), the organic layers werecombined, dried over anhydrous MgSO4 and filtered. The solventswere removed under reduced pressure to give a bright yellow solid,recrystallized from light petroleumto give the title compound 16 asa yellow powder (1.0 g, quant.), mp 47e48 C [Lit.36 mp 47 C]. nmax(film)/cm1 3054, 2985, 2226, 1605, 1487, 1421, 1369, 1265, 1212,1148, 1128, 1107, 961, 896, 828, 739, 705. 1H NMR (400 MHz, CDCl3):d 1.45 (s, 6H), 5.70 (d, 1H, J 11.6 Hz), 6.28 (d, 1H, J 11.6 Hz), 6.78(d, 1H, J 8.4 Hz), 7.24 (d, 1H, J 4.0 Hz), 7.37 (dd, 1H, J 8.4 Hz,4.0 Hz); 13C NMR (100 MHz, CDCl3): d 28.4, 77.9, 103.8, 117.2, 119.3,120.6, 121.7, 130.1, 132.2, 133.3, 156.8.

References:

Bulman Page, Philip C.;Chan, Yohan;Noor Armylisas, Abu Hassan;Alahmdi, Mohammed [Tetrahedron,2016,vol. 72,# 51,p. 8406 - 8416]

1740-74-5 Synthesis