Hydrochloric Acid → 4-Methyl-2-(methylamino)phenol

HRID 1032958Notes

Reaction equation

HRID 1032958 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([NH:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[OH:17])=O.C(OCC)(=O)C.Cl>CCOCC.O>[CH3:16][C:14]1[CH:13]=[CH:12][C:11]([OH:17])=[C:10]([NH:9][CH3:7])[CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 190269832-Formylamino-4-methylphenolHCID 21226445Aluminium lithium hydride

Product 1

HCID 126176884-Methyl-2-(methylamino)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminium hydride (3.56 g, 94 mmol) in dry ether (100 ml) was added dropwise a solution of the compound (1) (10.9 g, 72 mmol) in dry ether (600 ml) under ice-cooling. The mixture was stirred under ice-cooling for 30 minutes, and thereto was added ethyl acetate and water in that order. The aqueous layer was neutralized with diluted hydrochloric acid and extracted with ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel to give the title compound (2). Yield 7.63 g (77%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. extractionextracted with ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-97310a467a764b45af76aaee27f0f847
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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