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Properties of substance:

1,1-dichloroacetone

Group of substances:

organic

Physical appearance:

colorless liquid

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

C3H4Cl2O

Structural formula as text:

Cl2CHCOCH3

Molar/atomic mass: 126.96

Boiling point (°C):

120

Solubility (g/100 g of solvent):

diethyl ether: miscible [Ref.]
ethanol: soluble [Ref.]
water: difficulty soluble [Ref.]

Synthesis 1:

Reference: Gallucci, R. R., & Going, R. Chlorination of aliphatic ketones in methanol / Journal of Organic Chemistry. - 1981. - Vol. 46, No. 12 pp. 2537 [doi: 10.1021/jo00325a019]


CH3COCH3 + 2Cl2 → CH3COCHCl2 + 2HCl

Acetone, 6.2 g, was dissolved in 50 mL of DMF and allowed to react with 17.0 g of chlorine (~10% excess) which was bubbled into the reaction mixture from a trap cooled in a dry ice-acetone bath. The reaction mixture was cooled in an ice bath. The temperature was kept below 50 °C. Chlorine addition took ~2.0 h. The major product, 1,1-dichloroacetone, could be distilled directly from the crude reaction mixture, yield 17.9 g (64%).

Alternatively, the reaction could be worked up by extraction with 50 mL of carbon tetrachloride and 100 mL of 2 N HCl. The organic phase was washed two additional times with water and dried over anhydrous magnesium sulfate. Gas chromatographic mass spectral analysis showed only two products, 1,1-dichloroacetone and 1,1,1-trichloroacetone (95:5).

Reactions:

  1. [Ref.1]
    CH3COCHCl2 + 2K2CO3 → CH2=CHCOOK + 2KCl + KHCO3 + CO2
    CH2=CHCOOK + HCl → CH2=CHCOOH + KCl

References:

  1. CRC Handbook of Chemistry and Physics. - 95ed. - CRC Press, 2014. - pp. 3-156
  2. Dictionary of organic compounds. - vol.1, Abietic acid - Dypnone. - London, 1946. - pp. 732
  3. Свойства органических соединений: Справочник. - Под ред. Потехина А.А. - Л.: Химия, 1984. - pp. 322-323 [Russian]
  4. Справочник химика. - Т. 2. - Л.-М.: Химия, 1964. - pp. 908-909 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru