1,2-Dibromoethane → HCID 13688472, compound

Participants

Reaction Steps

4-[(Z)-1-Undecenyl]phenol, (2.30 g, 9.30 mmol) and anhydrous potassium carbonate, (1.93 g, 14.0 mmol) in methyl isobutyl ketone (100 ml) were stirred and treated with 1,2-dibromoethane, (5.27 g, 29 mmol). The mixture was refluxed for 24 h after which time a further aliquot of 1,2-dibromoethane, (5.27 g, 28 mmol) was added. The mixture was refluxed a further 24 h, then cooled and washed with water, (twice). The organic phase was dried, (MgSO4), and evaporated in vacuo to an oil. Purification by column chromatography on silica gel, eluting with n-hexane then dichloromethane gave 1.34 g (41%) of the title compound as a white crystalline solid mp 40°-1° C. νmax (mull) 1510, 1573 (weak) 1610 cm-1, δ (CDCl3) 0.86 (3H, distorted t, terminal CH3), 1.26 (14H, m, (CH2)7), 2.26 (2H, m, allylic CH2), 3.60 (2H, t, J 6 Hz, CH2Br), 4.26 (2H, t, J 6 Hz, OCH2) 5.56 (1H, d.t, Jd 12 Hz, Jt 7 Hz, =CH--alkyl), 6.32 (1H, d, J 12 Hz, ArCH=), 7.06 (4H, ABq, Δν 33 Hz, J 9 Hz, C6H4).

Provenance & Evidence