Thymol → 5-Amino-2-isopropylphenol

HRID 1805111

Reaction equation

HRID 1805111 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7](C)=[CH:6][C:5]=1[OH:11])([CH3:3])[CH3:2].C([O-])=O.[NH4+:15]>C(O)C.[Pd]>[NH2:15][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[C:5]([OH:11])[CH:6]=1

Participants

5

Reactant 2

HCID 6989ThymolHCID 2723923Ammonium formate

Product 1

HCID 598484345-Amino-2-isopropylphenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 2-isopropyl-5-methyl-phenol (1.3 g, 8.65 mmol) and ammonium formate (1.3 g, 20.62 mmol) in ethanol (50 mL) was added 10% Pd/C (887 mg, 8.33 mmol). The mixture was refluxed for an additional 5 minutes, cooled and filtered through a pad of celite. The solvent was removed by evaporation to give 5-amino-2-isopropylphenol which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.70 (s, 1H), 6.71 (d, J=8.1 Hz, 1H), 6.04 (d, J=2.2 Hz, 1H), 5.97 (dd, J=8.1, 2.2 Hz, 1H), 4.65 (s, 2H), 3.08-2.94 (m, 1H), 1.07 (d, J=6.9 Hz, 6H).

Workup

  1. temperatureThe mixture was refluxed for an additional 5 minutes
  2. temperaturecooled
  3. filtrationfiltered through a pad of celite
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-4f24dd476b5b4080b80a5ee2e9efcb84
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Linked notes

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