Acetone → HCID 68695897, compound

HRID 1175786Notes

Reaction equation

HRID 1175786 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[F:5][C:6]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[Cl-].[Na+].O>[F:5][C:6]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[CH:1][C:2](=[O:3])[CH:4]=[CH:8][C:7]1[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:6]=1[F:5]

Participants

6

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 1376642,3-Difluorobenzaldehyde

Product 1

HCID 68695897HCID 68695897, compoundYield 4.2%

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 0.5 g (8.61 mmol) of acetone and 2.51 g (17.65 mmol) of 2,3-difluoro benzaldehyde in 86 mL of a 0.25M solution of aqueous NaOH (21.52 mmol) was added 1.13 mL (0.86 mmol) of a 25% w/w aqueous solution of cetyltrimethylammonium chloride. The mixture was allowed to stir vigorously at room temperature for 48 hours, at which point it was diluted with 100 ml of brine and extracted with two 75 mL portions of methylene chloride. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was recrystallized from ethyl acetate to provide 110 mg (4%) of a yellow powder.

Workup

  1. extractionextracted with two 75 mL portions of methylene chloride
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-72ee159726884aff875fc23ea2c2fc6d
Source dataset
uspto-grants-2010_11
Patent number
US07842705B2

Reaction notes

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