2-Butene, 1-bromo-3-methyl- → 1-[3-(3-Methylbut-2-enyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanone

Participants

Reaction Steps

1-(3-Hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)-ethanone (0.125 g, 0.507 mmol) in DMSO (1 mL) was alkylated with 4-bromo-2-methyl-2-butene (0.106 g, 0.710 mmol, 0.082 mL) as described in Example 21. Aqueous workup gave 1-[3-(3-methylbut-2-enyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanone 0.201 g (100% crude) as a clear yellow crystalline solid: 1H-NMR (400 MHz, CDCl3) δ 7.72 (s, 1H, Ar-H), 6.83 (s, 1H, Ar-H), 5,48 (m, 1H, olefinic), 4.59 (d, J=6.6 Hz, 2H, OCH2), 2.60 (s, 3H, CH3), 1.79 (s, 3H, CH3), 1.76 (s, 3H, CH3), 1.67 (appp d, J=2.7 Hz, 4H, 2CH2), 1.28 (s, 6H, 2CH3), 1.26 (s, 6H, 2CH3).

Provenance & Evidence