4-Hydroxybenzaldehyde → HCID 22149821, compound

HRID 703366Notes

Reaction equation

HRID 703366 reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[F:10][C:9]([F:12])([F:11])[C:5]1[CH:6]=[C:7]([F:8])[C:2]([O:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 134215472,3-Difluoro-5-(trifluoromethyl)pyridine

Product 1

HCID 22149821HCID 22149821, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 36.6 g (0.20 mol) of 2,3-difluoro-5-(trifluoromethyl)pyridine in 150 ml of acetonitrile was added 25.6 g (0.21 mol) of p-hydroxybenzaldehyde, 29.0 g (0.21 mol) of powdered potassium carbonate and 50 mL of acetonitrile. The slurry was stirred at ambient temperature for 21 hours and then diluted with 300 mL of water. The organic layer was separated in a separatory funnel and washed twice with 150 mL portions of water followed by washing with 100 mL of a 10 percent potassium carbonate solution. The mixture was then dried over sodium sulfate and the solvent removed in vacuo leaving 48.0 g (84 percent of theoretical) of the above named compound, a light yellow oil, as the product; 1H NMR (CDCl3): 7.3-8.3 (m, 6H, Ar), 10.0 (s, 1H, CH(O).

Workup

  1. customThe organic layer was separated in a separatory funnel
  2. washwashed twice with 150 mL portions of water
  3. washby washing with 100 mL of a 10 percent potassium carbonate solution
  4. dry with materialThe mixture was then dried over sodium sulfate
  5. customthe solvent removed in vacuo
  6. customleaving 48.0 g (84 percent of theoretical) of the

Sources & evidence

ORD record
ord-6c75a683cb5544c5896d98fa1086aa44
Source dataset
uspto-grants-1991_01
Patent number
US04983211

Reaction notes

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