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ChemicalBook CAS DataBase List 3-Methyl-2-cyclohexen-1-one
1193-18-6

3-Methyl-2-cyclohexen-1-one synthesis

13synthesis methods
By acid hydrolysis and decarboxylation of the corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-1-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric acid.
-

Yield:1193-18-6 87%

Reaction Conditions:

with silver tetrafluoroborate;water in acetic acid at 110; for 10 h;regioselective reaction;

Steps:

24 4.2. General procedure for the synthesis of methyl ketones (2a-x). 4.2.24. 3-Methylcyclohex-2-enone (2x)
General procedure: To the mixture of terminal alkyne (1mmol), water (2.0 equiv), and acetic acid (2 mL), silver tetrafluoroborate (5 mol%) was added. The mixture was stirred at 110°C for 10 h. Water (10 mL) was added and the solution was extracted with ethyl acetate (3×8 mL), the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography to give the pure sample. 4.2.24. 3-Methylcyclohex-2-enone (2x). 1H NMR (400 MHz, CDCl3): δ=5.88 (s, 1H), 2.34 (t, J=6.8 Hz, 2H), 2.28 (t, J=6.4 Hz, 2H), 1.97-2.05 (m, 2H), 1.95 (s, 3H). 13C NMR (100 MHz, CDCl3): δ=199.9, 162.9, 126.6, 36.9, 30.9, 24.5, 22.5.

References:

Chen, Zheng-Wang;Ye, Dong-Nai;Qian, Yi-Ping;Ye, Min;Liu, Liang-Xian [Tetrahedron,2013,vol. 69,# 30,p. 6116 - 6120]

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