Sulfuric Acid → (R)-tert-Butyl 2-chloropropanoate

Participants

Reaction Steps

Prepared according to Wright et al. Tetrahedron Lett. 1997, 38, 7345. A 500 mL glass bomb was charged with magnesium sulfate (4.21 g, 35.0 mmol) and DCM (43.8 mL). To this suspension was added sulfuric acid (486 μL, 8.75 mmol), drop-wise with vigorous stirring. After 15 min of stirring, (R)-2-chloropropanoic acid (950 mg, 8.75 mmol) was added followed by tert-butanol (4.20 ml, 43.8 mmol). The bomb was sealed and stirred at rt for 19 h, whereupon sodium bicarbonate (aq satd, 100 mL) was carefully added, at which point all solids had dissolved. The layers were separated and the aqueous layer was extracted with DCM (2×). The combined organics layers were washed with brine, dried over Na2SO4 and concentrated in vacuo (20° C. bath, 50 mBar) to afford the title compound (1.36 g, 94%) as a light pink oil. 1H NMR (500 MHz, CDCl3) δ 4.29 (q, J=6.9 Hz, 1H) 1.65 (d, J=6.9 Hz, 3H) 1.49 (s, 9H).

Provenance & Evidence