Molecules 1999, 4, M122

3a,4,5,6,7,8,8a-Heptahydro-3-(4-chlorophenyl)cyclohept[d]isoxazole

Bruce A. Hathaway and Ryan A. Mueller

Department of Chemistry, Southeast Missouri State University, MS 6400, One University Plaza, Cape Girardeau, Missouri, 63701, USA. Tel. 001 573-651-2370; Fax 001 573-986-6433; E-mail: [email protected]

Received: 22 October 1999 / Accepted: 1 November 1999 / Published: 23 November 1999

To a solution of 4-chlorobenzaldehyde oxime ( 0.40g) in CH2Cl2 (10 mL) in a large test-tube were added 1.0 mL of cycloheptene and 3 drops of triethylamine. The solution was cooled to 5°C, then 7.0 mL of 5% NaOCl solution in water was added in small portions. After each portion was added, the test-tube was agitated with a VibromixerTM stirrer for 15 seconds. After the addition of all of the NaOCl solution, the test-tube was agitated with a VibromixerTM stirrer for 15 seconds every 5 minutes over the next hour. The reaction mixture was allowed to stand at least overnight. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (5 mL). The combined CH2Cl2 layers were evaporated to yield an off-white solid. The solid was recrystallized from methanol to yield shiny white plates. Yield: 0.26g (37%).

M.p. 97-97.5°C.

IR (KBr pellet, cm-1): 3085, 3070, 2930, 2909, 2871, 2854, 1593, 1494, 1469, 1402, 1383, 1343, 1091, 919, 899, 838.

1H-NMR (300MHz, CDCl3, ppm): 1.35-2.1 (10 H, multiplets), 3.68 (1H, m) , 4.87 (1H, m), 7.36 (2H, m), 7.59 (2H, m).

13C-NMR (75.5 MHz, CDCl3, ppm): 159.7, 136.0, 129.4, 128.7, 128.3, 85.6, 51.7, 31.5, 30.5, 28.6, 27.4, 24.1.

GC-MS (ion trap, m/e, in order of decreasing peak size): 137 (100%), 102, 50, 75, 139, 51, no molecular ion detected.

References and Notes
1. Gingrich, H. L.; Pickering, M. J. Chem. Educ. 1991, 68, 614-615. 
2. Bianchi, G.; De Micheli, C.; Gandolfi, R. J. Chem. Soc., Perkin Trans. 1 1972, 1711-1714. 

Sample Availability: available from MDPI.

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