Acetic Anhydride → HCID 22219471, compound

HRID 1793934Notes

Reaction equation

C(OC(=O)C)(=O)C.O[N:9]=[C:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][C:16]=1[N+:24]([O-:26])=[O:25])C(O)=O>C(O)(=O)C>[CH:21]([C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:10]#[N:9])=[C:16]([N+:24]([O-:26])=[O:25])[CH:17]=1)([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 1.18 mL of acetic anhydride in 5 mL of acetic acid was added a solution of 2.214 g of 2-hydroxyimino-3-(4-isopropyl-2-nitrophenyl)propionic acid in 5 mL of acetic acid at room temperature, and the mixture was stirred at 50° C. for 2 hours. After the reaction mixture was concentrated under reduced pressure, to the residue were added ethyl acetate and saturated aqueous sodium bicarbonate solution, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate, and the organic layers were combined. After being washed with water, and brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give 1.835 g of (4-isopropyl-2-nitrophenyl)acetonitrile.

Workup

concentrationAfter the reaction mixture was concentrated under reduced pressure, to the residue
additionwere added ethyl acetate and saturated aqueous sodium bicarbonate solution
customthe organic layer was separated
extractionThe aqueous layer was extracted with ethyl acetate
washAfter being washed with water, and brine
dry with materialthe organic layer was dried over anhydrous sodium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-687361a51d3c41f58673f0e79ab347ac
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022689B2

Reaction notes

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