Methanol → HCID 58374324, compound

HRID 79043Notes

Reaction equation

HRID 79043 reaction equation
[F:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([O:13][CH3:14])[CH:7]=[C:6]([F:15])[C:3]=1[CH:4]=[O:5].[C:16]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:27][OH:28]>>[CH3:27][O:28][CH:4]([O:5][CH3:16])[C:3]1[C:2]([F:1])=[C:9]([N+:10]([O-:12])=[O:11])[C:8]([O:13][CH3:14])=[CH:7][C:6]=1[F:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 583743662,6-Difluoro-4-methoxy-3-nitrobenzaldehyde

Product 1

HCID 58374324HCID 58374324, compoundYield 85%

Procedure

A mixture of 2,6-difluoro-4-methoxy-3-nitro-benzaldehyde (6.3 g, 29 mmol) in methanol (30 mL) with p-toluenesulfonic acid (110 mg, 0.58 mmol) was heated at reflux for 18 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate. The aqueous layer extracted with ethyl acetate and the combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a pale yellow solid (6.52 g, 85%). 1H NMR (CDCl3) 6.59 (1 H, dd, J=11.48, 2.08 Hz), 5.52 (1 H, s), 3.93 (3 H, s), 3.45 (6 H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate
  5. extractionThe aqueous layer extracted with ethyl acetate
  6. dry with materialthe combined organic extracts dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e01585e473cc4d38a1d7e9d0acfe411b
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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