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

HRID 618414Notes

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-aa69f3dfe56a49598d744caecb741e7a
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952386

Reaction notes

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