Chloroacetic Acid → HCID 13053832, compound

94.5g (1 mol) of chloroacetic acid and 154.7g of potassium bromide were put into a 1 liter four necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel. To the mixture were added 100 ml of water as a reaction medium and stirred vigorously. Then 127.4g (1.3 mol) of c.-- sulfuric acid were added droppwise over the course of an hour at a constant rate. During that time, the temperature of the reaction mixture rose to about 50° C. After the droppwise addition, stirring was continued for an hour at 55° C. Then 94.5g (1 mol) of 1-chloro-2-propanol and 200g of toluene were added to the reaction mixture, and refluxed for an hour at 100° ~ 110° C in an oil bath. A receiver was attached to a reflux condenser and water was removed from the reaction mixture by azeotropic distillation with toluene. Then the resultant crystals of potassium hydrogen sulfate were filtered off from the reaction mixture to give a toluene solution of 1-chloro-2-propyl bromoacetate, which was sufficient to use industrially as it is. But if needed, toluene was removed from the filtrate followed by distillating the residue to give 201.2g (93.4% of theory) of 1-chloro-2-propyl bromoacetate of bp 76° ~ 77° C (2 mmHg) as a colorless and clear liquid. nD25 = 1.4780, D420 = 1.5933. 176.6g (99.8%) of potassium hydrogen sulfate was isolated.

1. customequipped with a stirrer
2. customrose to about 50° C
3. additionAfter the droppwise addition
4. stirringstirring
5. waitwas continued for an hour at 55° C
6. temperaturerefluxed for an hour at 100° ~ 110° C in an oil bath
7. customA receiver was attached to a reflux condenser
8. customwater was removed from the reaction mixture by azeotropic distillation with toluene
9. filtrationThen the resultant crystals of potassium hydrogen sulfate were filtered off from the reaction mixture

ORD record

ord-dfc122d174c34adb836390868c783ddf

Source dataset

uspto-grants-1978_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04123443