Water → 2-Nitro-4-propanoylbenzoic acid

Temperature

110 °C

2-nitro-4-propionylbenzonitrile (5g) was suspended in acetic acid (15 ml), then water (5 ml) and concentrated sulfuric acid (5 ml) were added and the mixture was stirred at 110° C. for 6 hours 30 minutes. The reaction solution was gradually cooled down to room temperature, then water and a 5N aqueous sodium hydroxide solution were added, and the mixture was extracted with ethyl acetate. Next, the organic layer was extracted with water and 5N sodium hydroxide aqueous solution, then the obtained aqueous layer was adjusted by 50% sulfuric acid to pH 1. The resulting mixture was extracted with ethyl acetate. The obtained organic layer was concentrated in vacuo. Toluene was added to the concentrated residue which was then concentrated in vacuo to obtain a crude product of the title compound (4.6 g). The compound was used for the next process without purification.

1. temperatureThe reaction solution was gradually cooled down to room temperature
2. extractionthe mixture was extracted with ethyl acetate
3. extractionNext, the organic layer was extracted with water and 5N sodium hydroxide aqueous solution
4. extractionThe resulting mixture was extracted with ethyl acetate
5. concentrationThe obtained organic layer was concentrated in vacuo
6. additionToluene was added to the concentrated residue which
7. concentrationwas then concentrated in vacuo

ORD record

ord-74c64d15c5c64d3cb494ab3beb905476

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08049006B2