Trifluoroacetic acid → 3-Amino-2,4-dimethylphenol

HRID 1771636Notes

Reaction equation

HRID 1771636 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]([NH:9]C(=O)OC(C)(C)C)[C:5]([CH3:8])=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:9][C:4]1[C:3]([CH3:17])=[C:2]([OH:1])[CH:7]=[CH:6][C:5]=1[CH3:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89443943tert-butyl N-(3-hydroxy-2,6-dimethylphenyl)carbamate

Product 1

HCID 141306083-Amino-2,4-dimethylphenolYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-(3-hydroxy-2,6-dimethyl-phenyl)carbamate (657 mg, 2.8 mmol, 1.0 eq) in DCM (5 mL) was added TFA (5 mL) and the reaction stirred at room temperature overnight. The solvent was removed in vacuo. The residue was taken up in water and solution adjusted to pH 7 by addition of aqueous NaHCO3. The aqueous phase was extracted with EtOAc and the organic extract dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a yellow solid (370 mg, 97%) which was used without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. additionsolution adjusted to pH 7 by addition of aqueous NaHCO3
  3. extractionThe aqueous phase was extracted with EtOAc
  4. extractionthe organic extract
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6062873499df4af8bcd7e3e5a88e1a6b
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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