Sodium Bicarbonate → 4-Acetamido-3-hydroxyphenyl acetate

HRID 2112740Notes

Reaction equation

HRID 2112740 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]2[N:9]=[C:10]([CH3:12])[O:11][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=[O:18].O.C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([NH:9][C:10](=[O:18])[CH3:12])=[C:7]([OH:11])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 156622632-Methylbenzo[d]oxazol-6-yl acetateHCID 22392675Trifluoroacetic acid water

Product 1

HCID 688181524-Acetamido-3-hydroxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-1,3-benzoxazol-6-yl acetate (5.05 g, 28.8 mmol) in THF (100 mL) a mixture of trifluoroacetic acid/water (4 mL/10 mL) was added. The reaction mixture was stirred at room temperature for 16 hours, saturated aqueous NaHCO3 (150 mL) was added. The mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated in vacuo to give sub-title compound (4.0 g) as a crude product.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad3ad19dac9d46f0ba6b56b1395b4f67
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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