3-Bromobenzaldehyde → 3-(1-Tridecynyl)benzaldehyde

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Reaction of 3-bromobenzaldehyde with 1-tridecyne as described in example 3 gave 85% of the title compound after chromatography on silica, eluting with dichloromethane:petrol (bp 40:60) (1:3) νmax (neat) 2920, 2215, 1705, 1600, 1575, 1465, 1280, 1155, 795, and 680 cm-1, δ(CDCl3) 0.86 (3H, distorted t), 0.9-1.7 (18H, m), 2.4(2H, t, J=6 Hz), 7.7-7.9 (4H, m, aromatic), and 10.0 (1H, s, aldehyde). Analysed as the 2,4-dinitrophenylhydrazone m.p. 127° C. (recrystallized from acetic acid). Found, C, 67.27, H, 6.86; N, 12.01, C26H32N4O4 requires, C, 67.33, H, 6.79, N, 12.08%.

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