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

3a,4,5,6,7,8,9,9a-Octahydro-3-(4-chlorophenyl)cyclooct[d]isoxazole

by
Bruce A. Hathaway
*,
Forest G. Peltan
,
Ryan A. Mueller
and
Ryan M. Redfearn
Department of Chemistry, Southeast Missouri State University, MS 6400, One University Plaza, Cape Girardeau, Missouri, 63701, USA
*
Author to whom correspondence should be addressed.
Molecules 1999, 4(11), M123; https://doi.org/10.3390/M123
Submission received: 22 October 1999 / Accepted: 1 November 1999 / Published: 23 November 1999
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 04 m123 i001
To a solution of 4-chlorobenzaldehyde oxime (0.40g ) in CH2Cl2 (10 mL) in a large test-tube were added 1.0 mL of cyclooctene 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 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 95% ethanol to yield shiny white plates. Yield: 0.51g (75%).
M.p. 124-125°C.
IR (KBr pellet, cm-1): 3085, 3070, 1930, 2909, 2871, 2854, 1593, 1494, 1469, 1402, 1383, 1343, 1091, 919, 899, 838.
1H-NMR (300MHz, CDCl3, ppm): 1.2-2.2 (12 H, multiplets), 3.40 (1H, t, J=9.4 Hz), 4.50 (1H, m), 7.38 (2H, m), 7.61 (2H, m).
13C-NMR (75.5 MHz, CDCl3, ppm): 161.9, 136.0, 129.5, 128.6, 128.3, 86.2, 50.5, 30.6, 25.9, 25.8, 25.6, 25.2, 25.0.
GC-MS (ion trap, m/e, in order of decreasing peak size): 137 (100%), 102, 50, 75, 139, 51, no molecular ion detected.

Supplementary materials

Supplementary File 1Supplementary File 2

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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MDPI and ACS Style

Hathaway, B.A.; Peltan, F.G.; Mueller, R.A.; Redfearn, R.M. 3a,4,5,6,7,8,9,9a-Octahydro-3-(4-chlorophenyl)cyclooct[d]isoxazole. Molecules 1999, 4, M123. https://doi.org/10.3390/M123

AMA Style

Hathaway BA, Peltan FG, Mueller RA, Redfearn RM. 3a,4,5,6,7,8,9,9a-Octahydro-3-(4-chlorophenyl)cyclooct[d]isoxazole. Molecules. 1999; 4(11):M123. https://doi.org/10.3390/M123

Chicago/Turabian Style

Hathaway, Bruce A., Forest G. Peltan, Ryan A. Mueller, and Ryan M. Redfearn. 1999. "3a,4,5,6,7,8,9,9a-Octahydro-3-(4-chlorophenyl)cyclooct[d]isoxazole" Molecules 4, no. 11: M123. https://doi.org/10.3390/M123

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