Ammonium Acetate → 4-Hydroxy-2-methylbenzeneboronic acid

HRID 2423513Notes

Reaction equation

HRID 2423513 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH3:7][C:8]1[CH:9]=[C:10]([OH:23])[CH:11]=[CH:12][C:13]=1[B:14]1[O:18]C(C)(C)C(C)(C)[O:15]1.C([O-])(=O)C.[NH4+]>CC(C)=O.O>[OH:23][C:10]1[CH:11]=[CH:12][C:13]([B:14]([OH:18])[OH:15])=[C:8]([CH3:7])[CH:9]=1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 27734484-Hydroxy-2-methylbenzeneboronic acidYield 49%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Sodium periodate (2.39 g, 11.15 mmol) was added to 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (870.4 mg, 3.72 mmol) and ammonium acetate (859.8 mg, 11.15 mmol) in acetone and water (2:1, 36 mL) at room temperature. The mixture was stirred for sixty-eight hours, then filtered, and concentrated. Sodium chloride was added to the filtrate, and it was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:4 ethyl acetate:hexanes to give 275.7 mg (49%) of (4-hydroxy-2-methylphenyl)boronic acid as a solid. 1H NMR (400 MHz, d6-DMSO): δ 9.28 (s, 1H), 7.70 (d, J=9 Hz, 1H), 6.56-6.52 (m, 2H), 2.55 (s, 3H). ESI-LCMS m/z 151 (M−H)−.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionSodium chloride was added to the filtrate, and it
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-ee1b8e45dfc74f8bac26f206e75b1a25
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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