Synthesis of chloromethyl 2-chlorovinyl ketone

Preparation of chloromethyl 2-chlorovinyl ketone

Alternative Names: chloromethyl beta-chlorovinyl ketone; 1,4-dichloro-1-buten-3-one; 3-buten-2-one, 1,4-dichloro;

Preparation of chloromethyl 2-chlorovinyl ketone

Preparation of chloromethyl 2-chlorovinyl ketone

180 g of aluminum chloride are added gradually over 1 hour  with energetic stirring to 113 g of choroacetylchoride, and acetylene is passed in a rapid stream for 6 hours. During the reaction, the temperature is maintained at 25-35° C. When the reaction is complete the reaction mass is poured on to ice and extracted with ether. The obtained extract is dried over calcium chloride, the solvent is removed in vacuo, and the residue is vacuum distilled. The fraction boiling at 62-65° C  at 8-10 mm is collected, yielding 87.7 g (84% based on aluminum chloride or 65% based on chloroacetyl chloride). The pure substance boils at 58-59° C/7 mm or 73-79° C/15 mm.

Bulletin of the Academy of Sciences of the USSR, Division of chemical science; Vol 1, 1, 97-102, (1952)

IUPAC Name

1,4-dichlorobut-3-en-2-one

InChI

InChI=1S/C4H4Cl2O/c5-2-1-4(7)3-6/h1-2H,3H2

InChI Key

HFDIJTIPFVXOED-UHFFFAOYSA-N

Canonical SMILES

C(C(=O)C=CCl)Cl

Depositor-Supplied Synonyms

1,4-DICHLORO-3-BUTEN-2-ONE, 69711-44-0, 1,4-Dichloro-1-buten-3-one, CTK0E7216, HFDIJTIPFVXOED-UHFFFAOYSA-N, 3-Buten-2-one, 1,4-dichloro-, VZ34180, 3-Buten-2-one,1,4-dichloro-, (3E)-, 15787-79-8

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