1-Bromohexane → 1-(3-Hexyloxy-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 (0.103 g, 0.418 mmol) in DMSO (1 mL) was alkylated with bromohexane (0.097 g, 0.585 mmol, 0.082 mL) as described in Example 21. Aqueous workup gave 1(3-hexyloxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone 0.161 g (100% crude) as an orange oil: 1H-NMR (400 MHz, CDCl3) δ 7.74 (s, 1H, Ar-H), 6.82 (s, 1H, Ar-H), 4.02 (t, J=6.4 Hz, 2H, OCH2), 2.61 (s, 3H, CH3), 1.83 (m, 2H, CH2), 1.67 (app br d, 4H, 2CH2), 1.50 (m, 2H, CH2), 1.36 (m, 4H, 2CH2), 1.29 (s, 6H, 2CH3), 1.26 (s, 6H, 2CH3), 0.91 (t, J=7.0 Hz, 3H, CH3).

Provenance & Evidence