Potassium Hydroxide → HCID 68448777, compound

HRID 1516758Notes

Reaction equation

[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([C:13]([CH3:20])([CH3:19])[C:14]([O:16]CC)=[O:15])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]>CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:13]([CH3:20])([CH3:19])[C:14]([OH:16])=[O:15])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A 2N potassium hydroxide solution (18 ml) is added to a solution of ethyl 2-(3-chloro-4-nitrophenyl)-2-methylpropanoate (1 g) in methanol (20 ml) at a temperature of approximately 20° C. The mixture is then heated at 80° C. for 1.5 hours then cooled down to ambient temperature. The methanol is evaporated off by concentration of the mixture under reduced pressure. The remaining aqueous phase is washed with dichloromethane then cooled down to 0° C. and acidified by acetic acid. After the addition of dichloromethane, decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 and concentrated under reduced pressure in order to produce the expected compound in the form of an oil which crystallizes (852 mg, 95% yield).

Workup

temperaturethen cooled down to ambient temperature
customThe methanol is evaporated off by concentration of the mixture under reduced pressure
washThe remaining aqueous phase is washed with dichloromethane
temperaturethen cooled down to 0° C.
additionAfter the addition of dichloromethane, decantation and extractions
washthe combined organic phases are washed with salt water
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure in order

Sources & evidence

ORD record: ord-21abfe608c724d4087cb0f4da013f4fb
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227485B2

Reaction notes

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