1,2-Dichloroethane → 4-Oxo-5-hexenoic Acid

[cf. J. Chem. Soc., 3922 (1958)]. A mixture of aluminum chloride (66.7 g., 0.5 M), succinic anhydride (25 g., 0.25 M) and 1,2-dichloroethane (1 liter) in a 2 liter 3 neck flask equipped with a gas inlet tube, a mechanical stirrer and a drying tube is stirred rapidly and ethylene is bubbled in for 4.5 hours. This is poured into 900 ml. 5% hydrochlorc acid and ice. The layers are separated and the organic layer is washed with water and taken to dryness in vacuo. The aqueous layer is extracted with ether (300 ml.). This extract is washed with water and combined with the material from the original organic layer. After removal of solvent, 150 ml. of 10% potassium carbonate solution is added and the mixture is heated on a steam cone for 15 minute. After cooling, the product 4-oxo-5-hexenoic acid is extracted into ether, dried and freed of solvent in vacuo leaving 10.9 g. (34%) of brownish liquid which solidifies on standing. This is distilled to give 7.1 g. (22%) of colorless liquid which solidifies on standing, b.p. ~120°-130°/0.5 mm.

1. customequipped with a gas inlet tube, a mechanical stirrer and a drying tube
2. customethylene is bubbled in for 4.5 hours
3. additionThis is poured into 900 ml
4. customThe layers are separated
5. washthe organic layer is washed with water
6. extractionThe aqueous layer is extracted with ether (300 ml.)
7. washThis extract is washed with water
8. customAfter removal of solvent, 150 ml
9. additionof 10% potassium carbonate solution is added
10. temperaturethe mixture is heated on a steam cone for 15 minute
11. temperatureAfter cooling
12. extractionthe product 4-oxo-5-hexenoic acid is extracted into ether
13. customdried
14. customleaving 10.9 g
15. distillationThis is distilled
16. customto give 7.1 g

ORDレコード

ord-9c9ae727da254acf9be7b3d34eddd1a4

出典データセット

uspto-grants-1980_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04206137