Chloroacetyl chloride → HCID 11054894, compound

Temperature

0 °C

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:

1. temperatureThen the mixture was cooled to -5° C.
2. temperaturecooled again to -10° C
3. custom(exothermic reaction)
4. waitAgain after 0.5 hour finally a third portion each was instilled
5. additionadded
6. customTriethylammonium chloride precipitated during the addition of chloroacetyl chloride
7. additionAfter the final addition the mixture
8. stirringwas stirred 1.5 hours more at -5° C.
9. temperatureheated to room temperature
10. filtrationAfter another 3 hours the triethylammonium chloride was filtered off
11. washwashed with toluene
12. washThe filtrate was washed twice with 80 ml of 0.1M hydrochloric acid each
13. customThe combined organic phases were dried on magnesium sulfate
14. filtrationfiltered
15. concentrationconcentrated by evaporation on a rotary evaporator

ORD record

ord-99bfc6c1576b43bbb6c8064877e15a47

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05254756