4-Methylbenzyl chloride → 1-[3-(4-Methylbenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanone

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Reaction Steps

1-(3-Hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone (0.116 g, 0.471 mmol) was alkylated with 4-methylbenzylchloride (0.93 g, 0.659 mmol, 0.087 mL) as described in Example 21. Aqueous workup gave 1-[3(4-Methylbenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanone 0.217 g (131% crude) as a pale orange solid: 1H-NMR (400 MHz, CDCl3) δ 7.74 (s, 1H, ArH), 7.33 and 7.20 (d, of ABq, J=7.8 Hz, 4H, Ar-H), 6.91 (s, 1H, ArH), 5.08 (s, 2H, OCH2), 2.56 (s, 3H, CH3), 2.35 (s, 3H, ArCH3), 1.66 (br s, 4H, 2CH2), 1.28 (s, 6H, 2CH3), 1.25 (s, 6H, 2CH3).

Provenance & Evidence