2-Amino-o-cresol → 3-t-Butoxycarbonylamino-2-methylphenol

HRID 325031

Reaction equation

HRID 325031 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:10]([O:14][C:15](=O)[O:16]C(C)(C)C)([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([O:14][C:15]([NH:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 1044482-Amino-o-cresolHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 220334873-t-Butoxycarbonylamino-2-methylphenolYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-2-methylphenol (2.0 g; 16 mmol) and di-t-butylcarbonate were dissolved in THF (20 mL) and refluxed overnight. Evaporation of the solvent followed by flash chromatography (SiO2; EtOAc 5-30% in isohexane) afforded 2.48 g (69%) of the sub-title compound.

Workup

  1. temperaturerefluxed overnight
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-14d40c7fbec645dd81d48e97be74a956
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Linked notes

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