Acetic Acid → HCID 57424365, compound

HRID 1845817Notes

Reaction equation

HRID 1845817 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:5]=1[CH:6]=[O:7].[N+:13]([CH3:16])([O-:15])=[O:14].C(O)(=O)C>CO.C(OCC)C>[F:3][C:4]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:5]=1[CH:6]([OH:7])[CH2:16][N+:13]([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 1376632,5-Difluorobenzaldehyde

Product 1

HCID 57424365HCID 57424365, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To sodium hydroxide (1N, 3 L) and methanol (1500 mL) at 5° C. was added a solution of 2,5-difluorobenzaldehyde (350 g, 2.46 mol) and nitromethane (157 mL, 2.9 mol) in methanol (350 mL) dropwise over a period of 1 h. The reaction mixture was then neutralized with glacial acetic acid (165 mL). Diethyl ether (1500 mL) was added and the layers separated. The organic layer was washed successively with saturated aqueous sodium carbonate solution (1000 mL), and saturated aqueous brine (1000 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to afford 1-(2,5-difluorophenyl)-2-nitroethanol that was used without further purification in Step B.

Workup

  1. customthe layers separated
  2. washThe organic layer was washed successively with saturated aqueous sodium carbonate solution (1000 mL), and saturated aqueous brine (1000 mL)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5ddcfd357b084248a447cdb3281da92c
Source dataset
uspto-grants-2015_02
Patent number
US08951965B2

Reaction notes

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