Diethyl Ether → Methyl 5-hydroxy-2-nitrobenzoate

HRID 1439606Notes

Reaction equation

HRID 1439606 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].B(F)(F)F.[CH3:18]COCC.CCOCC>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:18])=[O:8]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8000Boron trifluoride etherateHCID 118825-Hydroxy-2-nitrobenzoic acid

Product 1

HCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Hydroxy-2-nitrobenzoic acid (47 g) in 750 ml methanol was treated with 160 ml BF3 -ether, ether distilled off until pot temperature reached 60°, and refluxed overnight. The procedure was repeated with 100 ml BF3 -ether. The mixture was poured into 3 volumes of water, extracted with ethyl acetate, the ethyl acetate washed with water, KHCO3 solution, water, dried and concentrated to give 48.4 g product.

Workup

  1. distillationdistilled off until pot temperature
  2. customreached 60°
  3. temperaturerefluxed overnight
  4. additionThe mixture was poured into 3 volumes of water
  5. extractionextracted with ethyl acetate
  6. washthe ethyl acetate washed with water, KHCO3 solution, water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dda6750317f4430b98da2a30faff6eb9
Source dataset
uspto-grants-1977_11
Patent number
US04060526

Reaction notes

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