4-(2,6-Dimethyl-4-nitro-phenoxy)-2-isopropyl-phenol → 4-(4-Amino-2,6-dimethyl-phenoxy)-2-isopropyl-phenol

HRID 584005Notes

Reaction equation

HRID 584005 reaction equation
[CH3:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[C:15]([CH3:22])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:12]([CH3:14])[CH3:13])[CH:6]=1>C(O)C.CCOC(C)=O.[Pd]>[NH2:19][C:17]1[CH:18]=[C:2]([CH3:1])[C:3]([O:4][C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:12]([CH3:14])[CH3:13])[CH:6]=2)=[C:15]([CH3:22])[CH:16]=1

Participants

5

Reactant 1

HCID 117796104-(2,6-Dimethyl-4-nitro-phenoxy)-2-isopropyl-phenol

Product 1

HCID 121141794-(4-Amino-2,6-dimethyl-phenoxy)-2-isopropyl-phenolYield 106.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2,6-dimethyl-4-nitro-phenoxy)-2-isopropyl-phenol (478 mg, 1.59 mmol) in a mixture of ethanol (10 mL) and EtOAc (30 mL) was added catalyst (10% Pd/C, 100 mg). The mixture was hydrogenated under 50 psi at RT for 2h. The mixture was filtered through Celite® and concentrated to give the title compound of Step C (458 mg) as a brown solid. The title product of Step C was used without further purification in the next step. MS (APCl−) Calc.: 271.2. Found: 270.2 (M−1).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-36fd3276809d4e88ae16f4234504c4ab
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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