Hydrochloric Acid → HCID 57879364, compound

HRID 1673556Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].C1(C)C=CC=CC=1.[C:12]([NH:20][C:21]1[CH:29]=[C:28]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37]C)[CH:32]=2)[CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(OCC)(=O)C>[C:12]([NH:20][C:21]1[CH:29]=[C:28]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=2)[CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24])(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

0.22 g of aluminum chloride was added to 1.0 ml of toluene solution containing 0.10 g of 2-(benzamido)-4-(3-methoxyphenoxy)benzoic acid at room temperature and stirred at 80° C. for 8 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/b hydrochloric acid were added. The organic layer was separated, and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate; acetic acid=15:10:1]to obtain 54 mg of 2-(benzamido)-4-(3-hydroxyphenoxy)benzoic acid as white solid.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe organic layer was separated
dry with materialdried over anhydrous magnesium sulfate
washafter washed with 1.0 mol/L hydrochloric acid
customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008

Sources & evidence

ORD record: ord-39f710366f964642a5775485be919889
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999132B2

Reaction notes

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