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Short Note

3a,4,5,6,7,8,9,10,11,12,13,13a-Dodecahydro-3-(4-chlorophenyl)cyclododeca[d]isoxazole

by
Bruce A. Hathaway
* and
Ryan A. Mueller
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), M121; https://doi.org/10.3390/M121
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 m121 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 cyclododecene 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 95% ethanol to yield shiny white flakes. Yield: 0.24g (29%).
M.p. 118-119°C.
IR (KBr pellet, cm-1): 2936, 2855, 1590, 1494, 1469, 1446, 1404, 1346, 1093, 901, 868, 832.
1H-NMR (300MHz, CDCl3, ppm): 1.35-1.65 (20 H, multiplets), 3.48 (1H, d of m), 4.76 (1H, d of m), 7.38 (2H, m), 7.64 (2H, m).
13C-NMR (75.5 MHz, CDCl3, ppm): 159.0, 136.0, 129.4, 128.5, 128.2, 84.5, 48.4, 31.9, 29.9, 27.3, 27.1, 24.0, 23.4, 23.0, 22.4, 22.06, 22.00.
GC-MS (ion trap, m/e, in order of decreasing peak size): 137 (100%), 102, 50, 75, 139, 51, very small molecular ion at 319/321 detected.

References

  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.; Mueller, R.A. 3a,4,5,6,7,8,9,10,11,12,13,13a-Dodecahydro-3-(4-chlorophenyl)cyclododeca[d]isoxazole. Molecules 1999, 4, M121. https://doi.org/10.3390/M121

AMA Style

Hathaway BA, Mueller RA. 3a,4,5,6,7,8,9,10,11,12,13,13a-Dodecahydro-3-(4-chlorophenyl)cyclododeca[d]isoxazole. Molecules. 1999; 4(11):M121. https://doi.org/10.3390/M121

Chicago/Turabian Style

Hathaway, Bruce A., and Ryan A. Mueller. 1999. "3a,4,5,6,7,8,9,10,11,12,13,13a-Dodecahydro-3-(4-chlorophenyl)cyclododeca[d]isoxazole" Molecules 4, no. 11: M121. https://doi.org/10.3390/M121

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