Toluene → (3-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-methyl Triphenylphosphonium Bromide

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Reaction Conditions

Reaction Steps

A solution of 2.58 g of 2-bromomethyl-3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene (from Example 6) and 1.94 g of triphenylphosphine in 50 ml of toluene was heated to reflux (oil bath at 115° C.) for 3 hours. The mixture was cooled to −5° C. for 1 hour and the white solid was filtered off. Concentration in vacuo of the filtrate gave a pale yellow residue, which was crystallized from toluene. The combined white solids were dried, giving 4.0 g of the title product. 1H NMR (CDCL3): 7.78 (m, 3H), 7.50-7.75 (m, 12 H), 6.95 (s, 1H), 6.90 (s, 1H), 5.14 (d, J=15 Hz, 2H), 1.76 (t, J=7.8 Hz, 2 H), 1.50-1.70 (m, 4 H), 1.22 (s, 6 H), 1.30-1.05 (m, 8 H), 0.85 (t, J=6.8 Hz, 3 H), 0.81 (s, 6 H).

Provenance & Evidence