Benzenesulfonyl chloride → HCID 86595248, compound

Participants

Reaction Conditions

Reaction Steps

A solution of citronellol 6 (30.0 g, 192 mmol) in 400 mL CH2Cl2 was allowed to stir at 0° C. under N2 in a 1 L round bottom flask. Triethylamine (60 mL, 430 mmol) was added in one portion, followed by DMAP (2.0 g, 1.64 mmol). Finally, benzenesulfonyl chloride (30 mL, 240 mmol) was added dropwise via syringe. After the mixture was stirred for 2 h at 0° C., it was partitioned between petroleum ether and, sequentially, 3 M aqueous HCl, water, and brine. The organic layer was dried (Na2SO4) and the solvent was removed in vacuo at 30° C. Removal of residual solvent under high vacuum yielded citronellyl benzenesulfonate (62.4 g, 110% of theoretical) as a clear yellow oil, TLC Rf(10% MTBE/petroleum ether)=0.41. 1H NMR (CDCl3) (δ): 7.92 (m, 2H), 7.66 (m, 1H), 7.56 (m, 2H), 5.03 (m, 1H), 4.09 (m, 2H), 1.91 (m, 2H), 1.68 (m, 1H), 1.67 (s, 3H), 1.57 (s, 3H), 1.52 (m, 1H), 1.44 (m, 1H), 1.24 (m, 1H), 1.11 (m, 1H), 0.81 (d, J=6.49 Hz, 3H); 13C NMR (CDCl3) (δ): u: 136.1, 131.4, 69.2, 36.6, 35.5, 25.1; d: 133.6, 129.1, 127.7, 124.2, 28.7, 25.6, 18.9, 17.5; IR (cm−1): 2914, 1449, 1360, 1188, 944.

Provenance & Evidence