Sodium Hydroxide → HCID 19387381, compound

HRID 2399280Notes

Reaction equation

C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([C:10]([CH3:17])([CH3:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=[CH:6][C:5]=1[O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[NH2:29].[OH-].[Na+]>O1CCCC1>[NH2:29][C:20]1[CH:21]=[C:22]([C:25]([F:26])([F:27])[F:28])[CH:23]=[CH:24][C:19]=1[O:18][C:5]1[CH:6]=[CH:7][C:8]([C:10]([CH3:17])([CH3:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][C:4]=1[C:3]([OH:30])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl-2-(2-amino-4-trifluoromethylphenoxy)-5-(1,1,3,3-tetramethylbutyl)benzoate (330 mg, 0.0008 mol) was mixed in tetrahyrofuran (15 mL) and cooled to 0° C. 1N Sodium hydroxide was added and stirring was continued, allowing the mixture to warm to room temperature. After 16 h the tetrahydrofuran was evaporated and the residue mixed in water. 3N Hydrochloric acid was added, bringing the pH to 4.0. The aqueous phase was extracted with ethyl acetate. The organic phase was dried (MgSO4) and the solvent was evaporated. The residue was flash chromatographed (silica gel, ethyl acetate/hexane) to yield the title compound. 1H NMR (250 MHz, CD3OD) δ7.97 (d, 1H), 7.54 (dd, 1H), 7.09 (d, 1H), 6.71-6.98 (m, 2H), 6.60 (d, 1H), 3.83 (s, 1H), 1.79 (s, 6H), 0.73 (s, 9H).

Workup

temperatureto warm to room temperature
customAfter 16 h the tetrahydrofuran was evaporated
additionthe residue mixed in water
addition3N Hydrochloric acid was added
extractionThe aqueous phase was extracted with ethyl acetate
dry with materialThe organic phase was dried (MgSO4)
customthe solvent was evaporated
customchromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-2a4ac4bf79214e58996ea59f4c4268b8
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05447957

Reaction notes

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