1.
The submitters used THF that was freshly distilled over Na/K alloy; NMP was distilled over CaH2. The checkers used commercially available anhydrous THF and NMP obtained from Aldrich Chemical Co. There appears to be a slight increase in yield when THF distilled from sodium/benzophenone ketyl is used instead of the commercial THF. All other solvents used were of reagent grade quality and were used without further purification.
2.
1,2-Dibromoethane, 1-bromononane (98%), 4-chlorobenzoic acid methyl ester (99%), and Fe(acac)3 (99.9%) were purchased from Aldrich Chemical Co. and used as received.
3.
The checkers found that a dark red oil separated upon concentration of the ethereal solution of the crude ester. In this instance, the ester was diluted with 200 mL of ether, washed with 200 mL of brine, and then again concentrated.
4.
The submitters obtained the product in 87-90% yield.
5.
The product is ≥ 95% pure by GC (Agilent 6890 Series, column: HP-5MS; 5% phenyl methyl siloxane, 30 m × 250 (m 0.25 (m); the remainder is octadecane formed by oxidative coupling of the Grignard reagent; T-program: 70°C (3.5 min)→280°C (20°C/min); 12.62 min retention time; 1H NMR (300 MHz, CDCl3): δ 0.86 (t, J = 6.7 Hz, 3H), 1.2-1.36 (m, 12H), 1.60 (m, 2H), 2.63 (t, J = 7.7 Hz, 2H), 3.88 (s, 3H), 7.22 (d, J = 8.4 Hz, 2H), 7.93 (d, J = 8.3 Hz, 2H); 13C NMR (75 MHz, CDCl3): δ 14.1, 22.7, 29.2, 29.3, 29.4, 29.7, 31.1, 31.9, 36.0, 51.9, 127.6, 128.4, 129.6, 148.5, 167.2; IR (film): 3032, 2953, 2926, 2855, 1725, 1611, 1465, 1435, 1278, 1178, 1109, 1021, 854 cm −1; MS (El): m/z (rel. Intensity) 262 (63, [M+]), 231 (24), 163 (13), 150 (100), 121 (8), 105 (9), 91 (41), 57 (8), 43 (13). Anal. Calcd for C17H26O2: C, 77.82; H, 9.99. Found C, 78.30; H, 10.45.
6.
The submitters obtained the product in 94% yield.
7.
The product has the following physical properties: mp 92.5-94.3°C; 1H NMR pdf(400 MHz, CDCl3): δ 0.86 (t, J = 6.9 Hz, 3H), 1.2-1.38 (m, 12H), 1.62 (m, 2H), 2.66 (t, J = 7.7 Hz, 2H), 7.26 (d, J = 8.2 Hz, 2H), 8.01 (d, J = 8.2 Hz, 2H); 13C NMR (100 MHz, CDCl3): δ 14.1, 22.7, 29.2, 29.3, 29.4, 29.5, 31.1, 31.8, 36.1, 126.7, 128.6, 130.4, 149.6, 171.9; IR (film): 3072, 2924, 2852, 2669, 2554, 1683, 1609, 1575, 1469, 1424, 1321, 1290, 945, 859, 758 cm −1; MS (El): m/z (rel. intensity): 248 (56, [M+]), 177 (7), 149 (9), 136 (100), 107 (9), 92 (38), 57 (14); 29 Anal. Calcd for C16H24O2-H2O: C, 72.14; H, 9.84. Found C, 72.53; H, 9.76.