Hydrochloric Acid → 3-(4-(Trifluoromethyl)benzamido)propyloxyphenol

HRID 377733

Reaction equation

C([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)(=O)C1C=CC=CC=1.CO.[OH-].[Na+].Cl>O>[F:29][C:28]([F:30])([F:31])[C:25]1[CH:26]=[CH:27][C:22]([C:21]([NH:20][CH2:19][CH2:18][CH2:17][O:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[OH:9])=[O:32])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 0.87 g of 3-ethyl-5-methyl-4-(3-(4-(trifluoromethyl)benzamido)propyloxyphenyl benzoate and 10 ml of methanol was added a mixture of 0.16 g of sodium hydroxide and 2 m of water, while stirring at 0° C. After stirring at room temperature for 24 hours, the reaction mixture was made weak acidic by the addition of 10% hydrochloric acid, and extracted with 50 ml of ethyl acetate. The ethyl acetate layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a residue. The residue was subjected to silica gel chromatography, which afforded 0.66 g of 3-ethyl-5-methyl-4-(3-(4-(trifluoromethyl)benzamido)propyloxyphenol (94% yield).

Workup

additionwas added
stirringAfter stirring at room temperature for 24 hours
extractionextracted with 50 ml of ethyl acetate
washThe ethyl acetate layer was washed with saturated saline solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto give a residue

Sources & evidence

ORD record: ord-c9f9246e641a4e2f953e6671c1253c70
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06028100

Linked notes

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