Methyl 3-methoxy-5-nitrobenzoate → (3-Methoxy-5-nitrophenyl)methanol

HRID 2071010Notes

Reaction equation

HRID 2071010 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1)[C:12](OC)=[O:13]>CCOCC>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1

Participants

4

Reactant 2

HCID 877382Methyl 3-methoxy-5-nitrobenzoateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 45091344(3-Methoxy-5-nitrophenyl)methanolYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminum hydride (0.1116 g, 2.94 mmol, 1.5 eq) was added to a stirred solution of methyl 3-methoxy-5-nitrobenzoate (0.408 g, 1.96 mmol, 1 eq) in 10 ml anhydrous Et2O at 0° C. under Ar. The reaction was stirred at 0° C. to room temperature overnight. Starting material was still present after stirring overnight. Additional LAH (0.1116 g, 2.94 mmol, 1.5 eq) was added. After 2 h the reaction was quenched with water. The reaction was diluted with saturated aqueous NaHCO3 and extracted with EtOAc (×2). The combined organics were washed with brine (×1) and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.2463 g (1.33 mmol, 68% yield) of (3-methoxy-5-nitrophenyl)methanol.

Workup

  1. stirringafter stirring overnight
  2. customAfter 2 h the reaction was quenched with water
  3. additionThe reaction was diluted with saturated aqueous NaHCO3
  4. extractionextracted with EtOAc (×2)
  5. washThe combined organics were washed with brine (×1)
  6. dry with materialdried over Na2SO4
  7. filtrationThe inorganics were filtered off
  8. customthe solvent was removed in vacuo
  9. customPurification via flash chromatography

Sources & evidence

ORD record
ord-a27c213b3e8c464f93de3c537d09a931
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…