Trifluoroacetic acid → 4-Acetamido-3-hydroxyphenyl acetate

HRID 270087Notes

Reaction equation

HRID 270087 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].C(=O)([O-])O.[Na+]>O1CCCC1>[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 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 156622632-Methylbenzo[d]oxazol-6-yl acetate

Product 1

HCID 688181524-Acetamido-3-hydroxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-methyl-1,3-benzoxazol-6-yl acetate (8.1 g, 42.3 mmol) was dissolved in tetrahydrofuran (60 mL), and trifluoroacetic acid (4 mL, 53.2 mmol) was added. The light brown solution was stirred over night at room temperature. Sodium hydrogen carbonate (aq, sat) was added, and the solution was extracted twice with ethyl acetate. The combined organic layers were concentrated to the titled compound (8.0 g, 91%) as a beige solid.

Workup

  1. extractionthe solution was extracted twice with ethyl acetate
  2. concentrationThe combined organic layers were concentrated to the titled compound (8.0 g, 91%) as a beige solid

Sources & evidence

ORD record
ord-d8dbe9912e804bef8afffdec1554dd7c
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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