Water → (E)-2-(7-chloro-3-methylhept-2-enyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

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Reaction Conditions

Reaction Steps

CAN (709 mg, 1.29 mmol) was dissolved into AcCN (7 mL) and water (3 mL) then cooled to 0° C. In a separate flask, (E)-1-(7-Chloro-3-methylhept-2-enyl)-2,5-dimethoxy-3,4,6-trimethylbenzene (175 mg, 0.53 mmol) was dissolved into AcCN (2 mL) and 1 drop of H2O and transferred to the stirring CAN solution. Stirring was maintained for 1 h, after which time an additional charge of CAN (350 mg) was added and let stir for 1 h. Water (10 mL) and EtOAc (10 mL) were added, the layers separated and the combined organics washed H2O (2×5 mL). The combined aqueous phases were back extracted using EtOAc (2×5 mL) and the combined organics washed with brine (2×5 mL), dried over anhydrous Na2SO4 and concentrated to a yellow oil. Flash chromatography (SiO2) yielded 29.7 mg of (E)-2-(7-chloro-3-methylhept-2-enyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione as a yellow oil (18.7%). 1H NMR (400 MHz, CDCl3) δ4.95 (t, J=6.8 Hz, 1H), 3.50 (t, J=6.8 Hz, 2H), 3.19 (d, J=6.8 Hz, 2H), 2.00 (m, 11H), 1.71 (m, 5H), 1.51 (m, J=7.2 Hz, 2H).

Provenance & Evidence