ChemicalBook CAS DataBase List 3-Hydroxy-2,6,6-triMethyl-1-cyclohexene-1-carbonitrile

3-Hydroxy-2,6,6-triMethyl-1-cyclohexene-1-carbonitrile synthesis

14synthesis methods

Product Name:3-Hydroxy-2,6,6-triMethyl-1-cyclohexene-1-carbonitrile
CAS Number:145106-79-2
Molecular formula:C10H15NO
Molecular Weight:165.23

1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile

264279-20-1
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3-Hydroxy-2,6,6-triMethyl-1-cyclohexene-1-carbonitrile

145106-79-2
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Yield:145106-79-2 77.3%

Reaction Conditions:

with sodium in methanol at 0 - 20;

Steps:

Preparation of Compound-6:

To a stirred solution of sodium (1.25 g, 54 mmol) in methanol(10 mL) at 0 °C was slowly added methanol (450 mL) followed by Compound-5 (30 g, 180mmol) in methanol (10 mL). The resulting solution was stirred at room temperature overnight,and then evaporated under vacuum. The residue was diluted with water, neutralized with acetic acid and extracted thrice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by column chromatography on 60-120 mesh silica gel and eluted with 20% ethyl acetate/petroleumether to obtain Compound-6 (23 g, 77.3%). MS (m/z): [M + H]+, 166.2.

References:

Zhang, Jianye;Dong, Zhiqian;Mundla, Sreenivasa Reddy;Hu, X. Eric;Seibel, William;Papoian, Ruben;Palczewski, Krzysztof;Golczak, Marcin [Molecular Pharmacology,2015,vol. 87,# 3,p. 477 - 491] Location in patent:supporting information