Methyl 2-methoxy-3-nitrobenzoate → (2-Methoxy-3-nitrophenyl)methanol

HRID 618243Notes

Reaction equation

HRID 618243 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-].[Na+]>C(O)(C)(C)C>[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

4

Reactant 2

HCID 590805Methyl 2-methoxy-3-nitrobenzoateHCID 4311764Sodium borohydride

Product 1

HCID 18789679(2-Methoxy-3-nitrophenyl)methanolYield 68.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 14.0 g of 2-methoxy-3-nitro-benzoic acid methyl ester in 245 ml of tert-butanol was treated with 6.75 g of sodium borohydride, and the heterogeneous mixture to 80° C. Methonol (62 ml) was slowly added at a dropwise rate over 2 hr. After 3 hr at 80° C., the solvent was evaporated at 40° C. under reduced pressure and the residue was treated with water, acidified with hydrochloric acid, extracted with ethyl acetate, the extracts washed with brine, dried, and evaporated to dryness. Purification of the residue by flash column chromatography on silica gel afforded 8.3 g of (2-methoxy-3-nitro-phenyl)-methanol as a brown solid. ##STR136##

Workup

  1. customto 80° C
  2. additionMethonol (62 ml) was slowly added at a dropwise rate over 2 hr
  3. customthe solvent was evaporated at 40° C. under reduced pressure
  4. additionthe residue was treated with water
  5. extractionextracted with ethyl acetate
  6. washthe extracts washed with brine
  7. customdried
  8. customevaporated to dryness
  9. customPurification of the residue by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b99fd020db97432ab6f9448d4b87eaff
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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