Sodium Hydroxide → 4-[2-[(E)-1-(4-tert-butylphenyl)ethylideneamino]oxyethoxy]-2-hydroxybenzoic acid

HRID 29647Notes

Reaction equation

HRID 29647 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][N:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=2)[CH3:16])=[CH:6][C:5]=1[OH:27].[OH-].[Na+]>C(O)C>[C:23]([C:20]1[CH:21]=[CH:22][C:17](/[C:15](=[N:14]/[O:13][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[C:5]([OH:27])[CH:6]=2)/[CH3:16])=[CH:18][CH:19]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 865973834-{2-[1-(4-Tert-butyl-phenyl)-ethylideneaminooxy]-ethoxy}-2-hydroxy-benzoic acid methyl ester

Product 1

HCID 113377114-[2-[(E)-1-(4-tert-butylphenyl)ethylideneamino]oxyethoxy]-2-hydroxybenzoic acidYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-{2-[1-(4-tert-butyl-phenyl)-ethylideneaminooxy]-ethoxy}-2-hydroxy-benzoic acid methyl ester (0.546 g, 1.29 mmol) in ethanol (10 mL) was added 1 M sodium hydroxide solution (2 mL, 2 mmol) and the reaction was heated at reflux for 40 minutes. After cooling to room temperature, it was concentrated to a small volume, acidified to pH 1 with 2M hydrochloric acid solution and extracted with ethyl acetate. The combined organics were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (30/70)+1% formic acid to afford the title compound (0.224 g, 47%) as a white solid. mp=157.4-158.7° C.; mass spectrum (+ESI, M+H) m/z 372. 1H NMR (400 MHz, DMSO-d6); δ 13.60 (bs, 1H), 11.50 (bs, 1H), 7.67 (d, 1H), 7.57 (d, 2H), 7.40 (d, 2H), 6.52 (m, 2H), 4.40 (t, 2H), 4.30 (t, 2H), 2.13 (s, 3H), 1.27 (s, 9H). Elemental analysis: Calcd. for C21H25NO5: C, 67.91; H, 6.78; N, 3.77, Found: C, 67.69; H, 6.81; N, 3.68.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 40 minutes
  3. concentrationit was concentrated to a small volume
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1ede8642cd764c89858064e0b581ccfb
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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