Acetone → HCID 54562802, compound

HRID 703365Notes

Reaction equation

HRID 703365 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([F:18])[C:6]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[OH-].[Na+].Cl.[CH3:24][C:25]([CH3:27])=[O:26]>O.C(Cl)Cl>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([F:18])[C:6]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[CH:24][C:25](=[O:26])[CH3:27])=[CH:12][CH:11]=2)=[N:7][CH:8]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22149821HCID 22149821, compound

Product 1

HCID 54562802HCID 54562802, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a slurry of 28.5 g (0.10 mol) of 4-(5-(trifluoromethyl)-3-fluoro-2-pyridyloxy)benzaldehyde in 250 mL of acetone and 250 mL of water was added 7.5 mL of 1N sodium hydroxide. The slurry was stirred at ambient temperature for 19 hours and then diluted with 300 mL of methylene chloride and 200 mL of water and made acidic to a pH of 2 with concentrated HCl. The organic layer was separated in a separatory funnel and washed with 500 mL of water and dried over sodium sulfate. The solvent was removed in vacuo leaving 32.5 g (100 percent of theoretical) of the above named compound, as the crude product. The above named product (melting at 71°-72.5° C.) was recovered in a yield of 27.9 g (85.8 percent of theoretical) after recrystallization of the crude product from hexane; Rf -0.19 (silica gel, 15:85 EtOAc:hexane), 1H NMR (CDCl3): δ 2.35 (s, 3H, --CH3), 6.65 (d, 1H, J=15 Hz, vinyl), 7.15-8.3 (m, 6H, ArH and vinyl).

Workup

  1. customThe organic layer was separated in a separatory funnel
  2. washwashed with 500 mL of water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customleaving 32.5 g (100 percent of theoretical) of the
  6. customwas recovered in a yield of 27.9 g (85.8 percent of theoretical)
  7. customafter recrystallization of the crude product from hexane

Sources & evidence

ORD record
ord-2376b8b46aee4d319b51faee87978e01
Source dataset
uspto-grants-1991_01
Patent number
US04983211

Reaction notes

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