Sodium Hydroxide → HCID 19387387, compound

HRID 2399294Notes

Reaction equation

HRID 2399294 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[NH2:23].[OH-].[Na+]>O1CCCC1>[NH2:23][C:14]1[CH:15]=[C:16]([C:19]([F:20])([F:21])[F:22])[CH:17]=[CH:18][C:13]=1[O:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:24])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19387380HCID 19387380, compound

Product 1

HCID 19387387HCID 19387387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-2-(2-amino-4-trifluoromethylphenoxy)-4-methoxybenzoate (13.0 g, 0.038 mol) was mixed in tetrahydrofuran and saponified with 1N sodium hydroxide. The solvent was evaporated and the residue mixed in water and acidified with 3N hydrochloric acid, bringing the pH to 4.0. The aqueous phase was extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The residue was flash chromatographed (silica gel, ethyl acetate/hexane/formic acid) to yield the title compound. 1H NMR (250 MHz, methanol d) δ8.00 (d, 1H), 7.10 (d, 1H), 6.88 (dd, 1H), 6.73-6.81 (m, 2H), 6.45 (d, 1H), 3.79 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue mixed in water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customchromatographed (silica gel, ethyl acetate/hexane/formic acid)

Sources & evidence

ORD record
ord-057d1ea484d042c2a4a1db9820036a4a
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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