Methyl 4-methylaminobenzoate → (4-(Methylamino)phenyl)methanol

HRID 63655

Reaction equation

HRID 63655 reaction equation
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 140375Methyl 4-methylaminobenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12128786(4-(Methylamino)phenyl)methanolYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(methylamino)benzoate (2.0 g, 12.1 mmol) in THF (30 mL) was added LAH (6.1 mL, 2.4 M in THF, 14.5 mmol) at 0° C. The reaction was stirred at r.t. for 2 h. The reaction was quenched with EtOAc (50 mL) and water (2 mL). The mixture was dried (Na2SO4) and concentrated. Purification by silica gel chromatography (PE:EtOAc=3:1) gave 1.0 g (60%) of the title compound as a yellow oil. [M+H] Calc'd for C8H11NO, 138. Found 138.

Workup

  1. customThe reaction was quenched with EtOAc (50 mL) and water (2 mL)
  2. dry with materialThe mixture was dried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (PE:EtOAc=3:1)

Sources & evidence

ORD record
ord-4e687493f3b24096abfc56565926ad9d
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Linked notes

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