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Properties of substance:

2-chloropropyl 3,5-dinitrobenzoate

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C10H9ClN2O6

Structural formula as text:

(O2N)2C6H3COOCH2CHClCH3

Molar/atomic mass: 288.64

Melting point (°C):

78-78.3

Synthesis 1:

Reference: Fickett, W., Garner, H.K., Lucas, H.J. The Configuration of Optically Active 1,2-Dichloropropane / Journal of the American Chemical Society. - 1951. - Vol. 73, No. 11 pp. 5067 [doi: 10.1021/ja01155a012]

In a 500-ml. flask were mixed 138 g. (0.60 mole) of freshly prepared 3,5-dinitrobenzoyl chloride and 57.5 g. (0.61 mole) of 2-chloro-1-propanol (prepared from propylene oxide; b.p. 70.3°/75 mm.). The reaction mixture was heated gradually to about 120° over a period of about 45 minutes, then to 140° for another 10 minutes. The mixture was cooled and poured into 500 ml. of dilute potassium carbonate solution, stirred until the mass solidified, collected by suction filtration and washed; weight, 167 g. (96% yield), m.p. 67—73°. Three recrystallizations from ethanol gave 100 g., m.p. 78.0—78.3°.

Anal. Calcd. for C10H9O6N2Cl: C, 41.59; H, 3.14; N, 9.70; Cl, 12.30. Found: C, 41.66; H, 3.19; N, 9.77; Cl, 12.30.

References:

  1. Journal of the American Chemical Society. - 1951. - Vol. 73, No. 11. - pp. 5067 [DOI: 10.1021/ja01155a012]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru