2,3-Difluoro-4-methoxybenzaldehyde → 2,3-Difluoro-4-hydroxybenzaldehyde

HRID 228412Notes

Reaction equation

HRID 228412 reaction equation
[F:1][C:2]1[C:9]([F:10])=[C:8]([O:11]C)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Cl.N1C=CC=CC=1>O>[F:1][C:2]1[C:9]([F:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 37449902,3-Difluoro-4-methoxybenzaldehydeHCID 10176127Pyridinium chloride

Product 1

HCID 231070632,3-Difluoro-4-hydroxybenzaldehydeYield 6,759.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

Combine 2,3-difluoro-4-methoxy-benzaldehyde (2.76 g, 16.0 mmol) and pyridine hydrochloride (18.5 g, 160 mmol) in a round bottom flask equipped with nitrogen inlet. Heat the mixture at 170° C. two hours, cool to near ambient temperature and dilute with water. Extract aqueous with EtOAc (2×), wash extract with 0.1 N aq. HCl (2×), water (2×) and brine, dry (MgSO4) and concentrate. Purify on silica gel (20% EtOAc/Hexane) to give 2,3-difluoro-4-hydroxy-benzaldehyde (171 g) as a yellow solid. 1HNMR (CDCl3): 10.18 (s, 1H), 7.59 (t, 1H), 6.90 (t, 1H), 6.14 (s, 1H).

Workup

  1. temperaturecool to near ambient temperature
  2. washExtract aqueous with EtOAc (2×), wash
  3. extractionextract with 0.1 N aq. HCl (2×), water (2×) and brine
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrate
  6. customPurify on silica gel (20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-7484f66ad95b40deb17c04628d9ecb83
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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