Chloroacetyl chloride → HCID 11054894, compound

Participants

Reaction Conditions

Reaction Steps

57.1 g (0.25 mol) of (2RS,3E)-4-iodo-3-buten-2-ol (86 percent, produced according to Example 2) was dissolved in 400 ml of toluene under argon, cooled to 0° C. and mixed with 2.4 g (20 mmol) of 4-(dimethylamino)pyridine. Then the mixture was cooled to -5° C., mixed with 11.07 g of triethylamine and cooled again to -10° C. After drop-by-drop addition of a first portion of 12.4 g of chloroacetyl chloride within 15 minutes (exothermic reaction) and another 0.5 hour of stirring, the same amounts of triethylamine and chloroacetyl chloride were instilled in succession. Again after 0.5 hour finally a third portion each was instilled, thus, altogether there were 33.21 g of triethylamine and 37.2 g chloroacetyl chloride added. Triethylammonium chloride precipitated during the addition of chloroacetyl chloride. After the final addition the mixture was stirred 1.5 hours more at -5° C. and then heated to room temperature. After another 3 hours the triethylammonium chloride was filtered off and washed with toluene. The filtrate was washed twice with 80 ml of 0.1M hydrochloric acid each. The aqueous phase was reextracted once with 50 ml of toluene. The combined organic phases were dried on magnesium sulfate, filtered and concentrated by evaporation on a rotary evaporator. The yield was 72.4 g (crude product, still contains some toluene). Further data on the product is:

Provenance & Evidence