1,3-Diphenyl-2-phenylsulfonylpropane

Mohammed Ramdani^a*, André Loupy^b and Alain Petit^b

^aLaboratoire de chimie organique et physique, Université Mohamed 1^er, Faculté des sciences, Oujda, Maroc. Fax (212)6 74 47 49 E-mail: [email protected]
^bLaboratoire des réactions sélectives sur supports, CNRS, UA 478, ICMO, Université Paris XI, bâtiment 410, 91405 Orsay cédex, France. Fax (33) 1 69 15 46 79 E-mail: [email protected]

Received: 28 June 1999 / Accepted: 2 July 1999 / Published: 20 August 1999
 
 

The product 2 was prepared from methyl phenylsulfonyl acetate in situ by the solid-liquid PTC conditions without solvent [1-5]. A mixture of the ester 1 (0.535 g, 2.5 mmol), benzyl chloride (0.791 g, 6.25 mmol), K₂CO₃ (0.862 g, 6.25 mmol) and 10 % of phase transfer catalyst Aliquat (0.1 g, 0.25 mmol) was placed in a pyrex tube which was then introduced into a Maxidigest MX 350 Prolabo microwave monomode reactor fitted with a rotational system. An approximate temperature of 130°C was measured at the end of the irradiation time (6 min with 140 w as irradiation power).The mixture was allowed to cool to ambient temperature. After dilution with ethyl acetate (30 ml) and subsequent filtration through Florisil^TM, the organic product was analysed by GC (using an internal standard) using a CPSIl, SCB - 25 m capillary column on a Carlo Erba CG 6000 (flame ionisation; gas carrier: He (70 Kpa); Temperatures (injector and detector): 280°C. Programmation in temperature: 200°C (1h) and 200-280°C (10°C / min)) and purified by recrystallization in diethyl ether (yield: 64 % of 2).

¹H NMR (CDCl₃): 2.8-2.9 (dd, 2H); 3.22-3.36 (dd, 2H); 3.58-3.68 (m, 1H); 6.8-7.2 (m, 10H); 7.45-7.9 (m, 5H).

IR (Nujol): 1310 and 1140 cm^-1 (SO₂).

MS (IC-NH₃, m / z): 354 (M⁺ + 18) / 100 %.

References

1. Loupy, A.; Pigeon, P.; Ramdani, M.; Jacquault, P. J. Chem. Research(S) 1993, 36-37.
2. Barnier, J. P.; Loupy, A.; Pigeon, P.; Ramdani, M.; Jacquault, P. J. Chem. Soc. Perkin Trans. 1 1993, 397-398.
3. (a) Krapcho, A. P. Synthesis1982, 805. (b) Krapcho, A. P. Synthesis 1982, 893.
4. Fujii, M.; Nakamura, K.; Mekata, H.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn. 1988, 61, 495-500.
5. Yuliang, W.; Yaozhong, J. Synth. Commun. 1992, 22, 2287-2291.

Sample Availability: Available from the authors.

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