CC1C=CC(S(Cl)(=O)=O)=CC=1.[CH2:12]([OH:18])[CH2:13][CH2:14][CH2:15][C:16]#[CH:17].N1C=CC=CC=1.CC1C=CC(S(OCCCCC#C)(=O)=O)=CC=1.[O:42]=[CH:43][C:44]1[CH:52]=[CH:51][C:49](O)=[C:46]([O:47][CH3:48])[CH:45]=1>C(Cl)Cl>[CH2:12]([O:18][C:49]1[CH:51]=[CH:52][C:44]([CH:43]=[O:42])=[CH:45][C:46]=1[O:47][CH3:48])[CH2:13][CH2:14][CH2:15][C:16]#[CH:17]
4-Methylbenzenesulfonyl chloride (2.9 g, 15 mmol), 5-hexyn-1-ol (1.1 mL, 10 mmol) and pyridine (1.6 mL, 20 mmol) in CH2Cl2 (10 mL) were treated according to Procedure 4 giving hex-5-ynyl 4-methylbenzenesulfonate (2.1 g, 83%) as a colourless oil. Vanillin (0.84 g, 5.6 mmol) was alkylated with hex-5-ynyl 4-methylbenzenesulfonate (2.1 g, 8.3 mmol) according to Procedure 4 and the crude product was recystallised from EtOAc/petrol to provide 4-(hex-5-ynyloxy)-3-methoxybenzaldehyde (0.80 g, 62%) as a colourless crystalline solid; mp 67-68° C.; δH (400 MHz, CDCl3) 1.74 (p, J=7.0 Hz, 2H, CH2), 1.97 (t, J=2.8 Hz, 1H, C≡CH), 2.02 (p, J=7.0 Hz, 2H, CH2), 2.30 (td, J=7.0, 2.8 Hz, 2H, CH2C≡CH), 3.92 (s, 3H, OCH3), 4.14 (t, J=7.0 Hz, 2H, OCH2), 6.97 (d, J5,6=8.0 Hz, 1H, H5), 7.41 (s, 1H, H2), 7.43 (d, J5,6=8.0 Hz, 1H, H6), 9.85 (s, 1H, CHO); δC (100 MHz, CDCl3) 18.1, 24.9, 27.9, 56.0, 68.5, 68.8, 83.9, 109.3, 111.4, 126.7, 130.0, 149.9, 154.0, 190.9; vmax 1029, 1269, 1584, 1681, 2956, 3246 cm−1.
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