Hydrochloric Acid → 1-Chloro-5-phenylpentan-2-one

4-Phenylbutanoyl chloride (14.7 g.) was added dropwise to a stirred solution of diazomethane (7.5 g.) in diethyl ether (340 ml.) at 0° C. The solution was stirred in an ice bath for 1 hour further and then it was saturated with anhydrous hydrogen chloride gas. After 1 hour at 0° C., dry nitrogen was passed through this solution, which was then poured onto crushed ice (about 300 ml.). The ethereal layer was separated and the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride, and extracted with diethyl ether. The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N), and then again with water, and dried over anhydrous magnesium sulphate. The solution was evaporated and the residue was distilled, to give 1-chloro-2-oxo-5-phenylpentane (11.5 g.), b.p. 150°-151° C./10 mm. Hg (Elemental analysis: C, 67.4; H, 7.1; Cl, 18.0%; C11H13ClO requires C, 67.2; H, 6.7; Cl, 18.0%. νmax 1455 cm-1, 1500 cm-1, 1725 cm-1).

1. waitAfter 1 hour at 0° C.
2. additionwas then poured
3. customThe ethereal layer was separated
4. additionthe aqueous phase was diluted with water (150 ml.), saturated with sodium chloride
5. extractionextracted with diethyl ether
6. washThe combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N)
7. dry with materialagain with water, and dried over anhydrous magnesium sulphate
8. customThe solution was evaporated
9. distillationthe residue was distilled

ORD record

ord-53ca491d13e7487289e92c0bcc36e202

Source dataset

uspto-grants-1980_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04183870