Potassium Hydroxide → HCID 68448777, compound

HRID 1784282Notes

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 solution of potassium hydroxide (18 ml) is added at a temperature of approximately 20° C. to a solution of ethyl 2-(3-chloro-4-nitrophenyl)-2-methylpropanoate (1 g) in methanol (20 ml). The mixture is then heated at 80° C. for 1.5 hours then cooled down to ambient temperature. The methanol is evaporated by concentration of the mixture under reduced pressure. The remaining aqueous phase is washed with dichloromethane then cooled down to 0° C. and acidified with 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 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-0f97eae317ad40e49923b9a79730dad9
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501524B2

Reaction notes

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