Menthyl Phenylsulfonyl Acetate

Mohammed Ramdani; Abderrahmane Elidrissi

doi:10.3390/M145

and

Laboratory of Chemistry Organic-Physic, Department of Chemistry, Faculty of Sciences, University of Mohammed The First, B P 524 - 60000 Oujda, Morocco

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Author to whom correspondence should be addressed.

Molecules2000, 5(4), M145;https://doi.org/10.3390/M145

This article belongs to the Section Molbank Section of Molecules, 1997-2001

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Menthyl phenylsulfonyl acetate was prepared from methyl phenylsulfonyl acetate by solid-liquid PTC trans-esterification conditions without a solvent [1]. To ester 1 (3.21 g, 15 mmol) was added (-)-menthol (3.05 g, 19.5 mmol), potassium carbonate (0.069 g, 3 mmol) and NBu₄HSO₄ (0.034 g, 0.6 mmol). The mixture was heated at 100 °C for 15 h in an oil bath under a dynamic vacuum, cooled to ambient temperature then treated with dilute HCl. The mixture was washed with aqueous NaCl and extracted with ethyl acetate. The product was purified by column chromatography on silica (eluent: pentane/ethyl acetate; 95/5), to give 2 (96%) as a colourless liquid.

¹H NMR (CDCl₃, 200 MHz): 8-7.5 (m, 5H, Ph); 4.7-4.53 (dt, 1H, CH-O); 4.1 (s, 1H, CH₂C=O); 0.95-0.78 (m, 6H, J = 7.2 Hz, 2(CH₃)_b); 0.75-0.62 (d, 3H, J = 7.2 Hz, (CH₃)_a).

¹³C NMR (CDCl₃, 50 MHz): 162 (CO₂); 139, 135, 130 and 129 (C_arom); 78 (CH₂); 61 (CH); 31 (CH₃).

IR: 1740 (CO₂); 1340 and 1130 (SO₂).

MS (IC-NH₃, m/z): 356 (M⁺ + 18, 100%).

Reference

Loupy, A.; Sansoulet, J.; Vaziri-Zand, F. Bull. Soc. Chim. Fr. 1987, 1027–1035, and references cited therein.

Sample Availability: Available from the authors.

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