Sulfuric Acid → Methyl 3-(2-nitrophenyl)prop-2-enoate

HRID 1919552

Reaction equation

[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([OH:10])=[O:9])([O-:3])=[O:2].S(=O)(=O)(O)O.[C:20](=O)(O)[O-].[Na+]>CO>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([O:10][CH3:20])=[O:9])([O-:3])=[O:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-nitrocinnamic acid (7) (10.38 g, 53.76 mmol) dissolved in methanol (200 ml) was dropped a small amount of concentrated sulfuric acid at room temperature, and the reaction mixture was stirred at 70° C. for 12 hours. After the reaction was completed, the resulting solution was basified with a saturated aqueous solution of sodium bicarbonate to weak basicity and extracted with dichloromethane three times. Then, the organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate:hexane=1:5) to give the target compound (11.03 g, 99%).

Workup

extractionextracted with dichloromethane three times
dry with materialThen, the organic phase was dried with anhydrous magnesium sulfate
distillationdistilled under reduced pressure

Sources & evidence

ORD record: ord-c1436bb127a94893a4c68dc8296ea40f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168646B2

Linked notes

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