2-Methyl-2-(4-nitrophenyl)-1,3-propanediol → 2-(4-Aminophenyl)-2-methylpropane-1,3-diol

HRID 1842971Notes

Reaction equation

HRID 1842971 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)([CH2:5][OH:6])[CH2:3][OH:4]>C(O)C.[Pd]>[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:2]([CH3:1])([CH2:5][OH:6])[CH2:3][OH:4])=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 136636512-Methyl-2-(4-nitrophenyl)-1,3-propanediol

Product 1

HCID 594100922-(4-Aminophenyl)-2-methylpropane-1,3-diolYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 2-methyl-2-(4-nitrophenyl)propane-1,3-diol (1.2 g, 5.68 mmol, 1.0 eq) in ethanol (30 mL) was added 10% Pd/C (300 mg) and the mixture was stirred under hydrogen gas balloon atmosphere for 5 h at RT. The reaction mixture was filtered through celite pad and filtrate concentrated under vacuum to get 2-(4-aminophenyl)-2-methylpropane-1,3-diol (1 g, 97%; TLC system: chloroform/MeOH (9:1); Rf: 0.3).

Workup

  1. filtrationThe reaction mixture was filtered through celite pad and filtrate
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-12666dbd964640fab7b7ffbae1753de2
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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