Pyridine → HCID 13138782, compound

Participants

Reaction Steps

step 1—To a solution of 1,4-cyclohexanediol (20.0 g, 172 mmol) and pyridine (100 mL) cooled to 0° C. was added dropwise over 2 h a solution of 32.0 g (168 mmol)p-toluenesulfonyl chloride in CHCl3 (100 mL). After the addition was complete the reaction mixture was stirred at RT for 17 h. The solvent was evaporated in vacuo and the residue was taken up in refluxing toluene and petroleum ether was added until the solution became cloudy. The mixture was cooled and the supernatant was decanted. The remaining solid was dissolved in DCM and vacuum filtered through a pad of SiO2. The filter cake was washed with a mixture of DCM/MeOH (95:5). The dark golden oil was dried under vacuum to afford 35.6 g (78%) of toluene-4-sulfonic acid 4-hydroxy-cyclohexyl ester (76) contaminated with a small amount of bis-tosylate: 1H NMR (CDCl3, 300 MHz): δ 7.79 (dd, 2H), 7.73 (dd, 2H), 4.64-4.48 (m, 1H), 3.75-3.69 (m, 1H), 2.45 (s, 3H), 1.95-1.83 (m, 3H), 1.70-1.26 (m, 6H).

Provenance & Evidence