Borane → (2-Methyl-4-nitrophenyl)methanol

HRID 469836Notes

Reaction equation

HRID 469836 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1.B.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 6331BoraneHCID 11430Potassium CarbonateHCID 747904-Nitro-o-toluic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 21345674(2-Methyl-4-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.08 g (27.2 mmol) 2-methyl-4-nitrobenzoic acid in 50 ml dry THF, 41 ml (41 mmol) borane-THF complex (1M solution in THF) is added drop-wise at 0° C. After completion of the borane addition, the reaction mixture is stirred at room temperature for 20 h. After that a K2CO3 solution (1.33 g in 49 ml water) is slowly added under stirring. Then the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is taken up in diethylether, vigorously stirred, and the title compound is obtained after filtration as a yellow crystalline solid.

Workup

  1. stirringunder stirring
  2. additionThen the reaction mixture is poured on water
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic layers are washed with water and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. stirringvigorously stirred

Sources & evidence

ORD record
ord-76c24169e53a4c4699c20463670903bc
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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