Sodium Hydroxide → 4-(Morpholin-3-on-4-yl)-3-trifluoromethyl-benzoic acid

HRID 2094243Notes

Reaction equation

[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[C:16]([F:19])([F:18])[F:17])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].[Mn]([O-])(=O)(=O)=[O:23].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[C:16]([F:17])([F:19])[F:18])[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:23]

Participants

Conditions

Temperature: 45 °C

Procedure

1.00 g (3.63 mmol) 4-(morpholin-4-yl)-3-trifluoromethyl-benzoic acid (prepared by synthesis sequence analogously to Example 13a and 13b) is suspended in 40 ml of water and 150 mg (3.75 mmol) sodium hydroxide are added. Then 1.73 g (10.92 mmol) potassium permanganate are added and the mixture is stirred for 1.5 hours at 45° C. Then the reaction mixture is cooled in the ice bath and sodium thiosulphate is added until total decolorisation is obtained. After extraction 3 times with ethyl acetate the combined organic phases are dried over sodium sulphate evaporated down i. vac. After application of the residue to silica gel it is purified by chromatography on silica gel (eluant: dichloromethane/methanol 95:5).

Workup

additionis added until total decolorisation
customis obtained
extractionAfter extraction 3 times with ethyl acetate the combined organic phases
dry with materialare dried over sodium sulphate
customevaporated down i
customAfter application of the residue to silica gel it is purified by chromatography on silica gel (eluant: dichloromethane/methanol 95:5)

Sources & evidence

ORD record: ord-49bf3b45d9694c9ab66abc996ec792c0
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445525B2

Reaction notes

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