Methanol → Methyl 6-Bromohexanoate

Participants

Reaction Steps

As mentioned in the general procedure (I), 6-bromohexanoic acid (15 g, 76.9 mmol, 1 equiv) was dissolved in methanol (150 mL), and a catalytic amount of conc.H2SO4 (2 mL) was added and the reaction was carried out. The product was taken to next step without column purification. Yield 14.8 g (92%). 1H NMR (400 MHz, CDCl3): δ 3.66 (s, 3H), 3.42-3.38 (m, 2H), 2.32 (t, J=7.2 Hz, 2H), 1.90-1.83 (m, 2H), 1.68-1.61 (m, 2H), 1.50-1.44 (m, 2H). 13C NMR (100 MHz, CDCl3); δ 173.9, 51.5, 33.8, 33.4, 32.3, 27.6, 24.0. EI/MS m/z (r.i.) 211(M+2, 98), 210(M+1, 8), 209(M+, 100), 178(16), 161(33), 129(51), 97(28), 87(9), 74(23), 69(23).

Provenance & Evidence