Next Article in Journal
Menthyl 2-Benzyl-2-phenylsulfonyl Acetate
Previous Article in Journal
6-S-Trityl-mercapto-hexan-1-ol
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

Menthyl Phenylsulfonyl Acetate

Laboratory of Chemistry Organic-Physic, Department of Chemistry, Faculty of Sciences, University of Mohammed The First, B P 524 - 60000 Oujda, Morocco
*
Author to whom correspondence should be addressed.
Molecules 2000, 5(4), M145; https://doi.org/10.3390/M145
Submission received: 21 December 1999 / Accepted: 14 January 2000 / Published: 28 April 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m145 i001
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 (Carom); 78 (CH2); 61 (CH); 31 (CH3).
IR: 1740 (CO2); 1340 and 1130 (SO2).
MS (IC-NH3, m/z): 356 (M+ + 18, 100%).

Reference

  1. Loupy, A.; Sansoulet, J.; Vaziri-Zand, F. Bull. Soc. Chim. Fr. 1987, 1027–1035, and references cited therein.
Sample Availability: Available from the authors.

Share and Cite

MDPI and ACS Style

Ramdani, M.; Elidrissi, A. Menthyl Phenylsulfonyl Acetate. Molecules 2000, 5, M145. https://doi.org/10.3390/M145

AMA Style

Ramdani M, Elidrissi A. Menthyl Phenylsulfonyl Acetate. Molecules. 2000; 5(4):M145. https://doi.org/10.3390/M145

Chicago/Turabian Style

Ramdani, Mohammed, and Abderrahmane Elidrissi. 2000. "Menthyl Phenylsulfonyl Acetate" Molecules 5, no. 4: M145. https://doi.org/10.3390/M145

Article Metrics

Back to TopTop