Ethylene Glycol → HCID 14834700, compound

Temperature

65 °C

Compound VI was made as follows: ethylene glycol (310.0 g, 5.00 moles) was heated to 60° C. before beginning the dropwise addition of 2-chloropropanoyl chloride (127.0 g, 1.00 mole) dissolved in 300 ml of anhydrous diethyl ether. The reaction was exothermic and the temperature rose to 65° C. The ether was allowed to boil off throughout the reaction. The reaction was heated to maintain 65° C. throughout the latter part of the addition and for 30 minutes after completion. The reaction solution was separated into two 250 ml batches that were added separately to 400 ml of H2O and extracted three times with 200 ml of hexane. The hexane extract was discarded and the aqueous phase was saturated with potassium chloride and extracted three times with 200 ml of ethyl acetate. The ethyl acetate was evaporated in vacuo and the concentrate was diluted with 300 ml of diethyl ether and dried over a mixture of anhydrous potassium carbonate and magnesium sulfate. After removing the solvent, the oil was vacuum distilled to give 109.4 g (71.0% yield) of approximately 95% pure 2-hydroxyethyl-2-chloropropanoate. The colorless, clear liquid had a boiling point of 85°-87° C./0.20 mm Hg. The structure of the compound was in agreement with the following data:

1. customrose to 65° C
2. customto boil off throughout the reaction
3. temperatureThe reaction was heated
4. customThe reaction solution was separated into two 250 ml batches that
5. additionwere added separately to 400 ml of H2O
6. extractionextracted three times with 200 ml of hexane
7. extractionThe hexane extract
8. extractionextracted three times with 200 ml of ethyl acetate
9. customThe ethyl acetate was evaporated in vacuo
10. additionthe concentrate was diluted with 300 ml of diethyl ether
11. dry with materialdried over a mixture of anhydrous potassium carbonate and magnesium sulfate
12. customAfter removing the solvent
13. distillationdistilled

ORD record

ord-6fd64d827f1c4e9ca360f15f26327408

Source dataset

uspto-grants-1990_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04908381