2-Methylbenzyl alcohol → HCID 45792126, compound

Participants

Reaction Steps

To a solution of 2-methylbenzyl alcohol (100 g, 0.82 mol) and diisopropylethylamine (171 mL, 0.98 mol) in CH2Cl2 (400 mL) at -5° C. was added dropwise methanesulfonyl chloride (74 mL, 0.95 mmol) with stirring under argon. After 1 hr at -5° and 3 hr at 20° C., this solution was added dropwise simultaneously with diisopropylethylamine (428 mL, 2.46 mol) to a slurry of glycine methyl ester hydrochloride (308.8 g, 2.45 mol) in DMF (400 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature for overnight, then treated slowly with satd NaHCO3 solution (1 L) and EtOAc (1 L). The layers were separated, the aqueous washed with EtOAc, and the organics combined, washed with satd NaHCO3 solution, brine, and dried (MgSO4). This solution was filtered, cooled to 0° C., and HCl was bubbled into the solution to precipitate the title compound. 1H NMR (CDCl3) δ 7.61 (d, 1H, J=7 Hz), 7.7-7.8 (m, 3H), 4.31 (s, 2H), 3.77 (s, 3H), 3.65 (s, 2H), 2.46 (s, 3H).

Provenance & Evidence