Hydrochloric Acid → HCID 86679083, compound

Temperature

10 °C

To a stirred solution of 2-(2,4-dichloro-benzyl)-malonic acid diethyl ester (6.4 g; 20 mmol) in methanol (30 ml) under argon at 23° C., was added dropwise a solution of sodium methoxide 5.4 M in methanol (4.3 ml; 23 mmol), resulting in a small exothermic (25° C.) reaction. After addition the reaction mixture was cooled to 10° C. Isoamyl nitrite (3.2 ml; 22 mmol) was added dropwise to the cooled mixture (temperature kept below 15° C.). The mixture was stirred for 2 hours at 10° C. and 1 h at 23° C. 2 N hydrochloric acid (10 ml) was added to the mixture which was stirred at 23° C. for 30 min. The reaction mixture was then poured in brine (200 ml) and extracted with ethyl acetate (3×100 ml). Combined organics were dried over sodium sulfate and evaporated under reduced pressure to give the crude solid which was recrystallized at 5° C. from cyclohexane to afford 2.5 g (48% of theory) of 3-(2,4-dichloro-phenyl)-2-(hydroxyimino)-propionic acid methyl ester as a white powder (melting point: 97-100° C.).

1. customresulting in a small exothermic (25° C.) reaction
2. additionAfter addition the reaction mixture
3. stirringwas stirred at 23° C. for 30 min
4. extractionextracted with ethyl acetate (3×100 ml)
5. dry with materialCombined organics were dried over sodium sulfate
6. customevaporated under reduced pressure
7. customto give the crude solid which
8. customwas recrystallized at 5° C. from cyclohexane

ORD record

ord-2b751544e19642b19f886983958046b1

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552049B2