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Volume 2007
Issue 3
10.3390/M552
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Short Note

3-(2-Oxopropyl)-2(3H)-benzoxazolone

by
Ognyan I. Petrov
*,
Yordanka B. Ivanova
,
Mariana S. Gerova
and
Katya V. Petrova
Sofia University, Faculty of Chemistry, Department of Applied Organic Chemistry, 1 James Bourchier Ave., 1164 Sofia, Bulgaria
*
Author to whom correspondence should be addressed.
Molbank 2007, 2007(3), M552; https://doi.org/10.3390/M552
Submission received: 9 March 2007 / Accepted: 19 March 2007 / Published: 30 May 2007
Versions Notes

Molbank 2007 m552 i001
The title compound is an important intermediate for the preparation of 3,4- and 3,4,5-substituted 1-(2-hydroxy-phenyl)imidazolin-2-ones [1,2] and 6-methyl-4-(2-hydroxyphenyl)-1,2,4-triazin-3-ones [3]. According to literature data, the product 3 is prepared from 2(3H)-benzoxazolone with commercially unavailable bromoacetone in abs. ethanol in the presence of sodium ethoxide [4,5]. We present an improve method for the synthesis of 3-(2-oxopropyl)-2(3H)-benzoxazolone (3) from available starting materials 1 and 2 under PTC conditions in higher yield.
To a mixture of 2(3H)-benzoxazolone (6.75 g, 50 mmol), fine powdered potassium carbonate (4.14 g, 30 mmol) and TEBA (200 mg) in DMF (15 ml), chloroacetone (4 ml, 50 mmol) was added. The reaction mixture was stirred for 1 h at 20-25 0C and then poured under stirring into 150 ml of water. The resulting precipitate was filtered and washed with water. Recrystallization from ethanol gave the product 3 as colorless needles. Yield: 90%.
Melting point: 119-120 0C
Elemental Analysis: Calculated for C10H9NO3: C 62.82%, H 4.74%, N 7.33%. Found: C 62.95%, H 4.53%, N 7.17%.
IR (nujol, cm-1): 1770, 1720 (CO).
1H-NMR (250 MHz, CDCl3): 2.25 (s, 3H, CH3); 4.61 (s, 2H, CH2); 6.77-7.21 (m, 4H, arom. H).
13C-NMR (63 MHz, CDCl3): 26.9 (CH3CO); 50.7 (CH2CO); 108.2 (C7); 109.9 (C4); 122.7 (C5); 123.8 (C6); 142.4 (C7a); 154.3 (C2); 199.8 (CH2CO).
MS (m/z, %): 191 [M+] (47); 148 (67); 120 (12); 104 (11); 77 (100); 65 (10); 50 (19).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Lozanova, Ch.; Kalcheva, V.; Simov, D. Khim. Geterosikl. Soedin. 1988, 10, 1362.
  2. Lozanova, Ch.; Kalcheva, V. J. Prakt. Chem. 1989, 331(6), 1007.
  3. Bojtscheva, Ch.; Simov, D.; Kaltscheva, V. J. Prakt. Chem. 1979, 321(2), 226.
  4. Zinner, H.; Randow, F. J. Prakt. Chem. 1961, 4, 144.
  5. Simov, D. A.; Kalcheva, V.B.; Boycheva, H.S. Compt. Rend. Acad. Bulg. Sci. 1974, 27, 1073.

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MDPI and ACS Style

Petrov, O.I.; Ivanova, Y.B.; Gerova, M.S.; Petrova, K.V. 3-(2-Oxopropyl)-2(3H)-benzoxazolone. Molbank 2007, 2007, M552. https://doi.org/10.3390/M552

AMA Style

Petrov OI, Ivanova YB, Gerova MS, Petrova KV. 3-(2-Oxopropyl)-2(3H)-benzoxazolone. Molbank. 2007; 2007(3):M552. https://doi.org/10.3390/M552

Chicago/Turabian Style

Petrov, Ognyan I., Yordanka B. Ivanova, Mariana S. Gerova, and Katya V. Petrova. 2007. "3-(2-Oxopropyl)-2(3H)-benzoxazolone" Molbank 2007, no. 3: M552. https://doi.org/10.3390/M552

APA Style

Petrov, O. I., Ivanova, Y. B., Gerova, M. S., & Petrova, K. V. (2007). 3-(2-Oxopropyl)-2(3H)-benzoxazolone. Molbank, 2007(3), M552. https://doi.org/10.3390/M552

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