Trimethyl borate → (2-Methoxy-3-nitrophenyl)methanol

HRID 1861956Notes

Reaction equation

HRID 1861956 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[O:13][CH3:14].[BH4-].[Li+].B(OC)(OC)OC>O1CCCC1>[CH3:14][O:13][C:5]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 590805Methyl 2-methoxy-3-nitrobenzoateHCID 4148881Lithium borohydride

Product 1

HCID 18789679(2-Methoxy-3-nitrophenyl)methanolYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methoxy-3-nitrobenzoic acid methyl ester (4.82 g), lithium borohydride (298 mg), trimethyl borate (0.27 ml) and anhydrous tetrahydrofuran (200 ml) was heated under reflux for 5 h. The reaction mixture was distilled under reduced pressure and ethyl acetate and water were added to the resulting residue. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1) to give 3.18 g of the titled compound (yield, 76%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. distillationThe reaction mixture was distilled under reduced pressure and ethyl acetate and water
  4. additionwere added to the resulting residue
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b7f432aefc3d4a9da316f54fa294f86b
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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