Acetone → HCID 5709173, compound

HRID 2113935Notes

Reaction equation

HRID 2113935 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=O.[CH3:11][C:12]([CH3:14])=[O:13].[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1/[CH:4]=[CH:11]/[C:12](=[O:13])/[CH:14]=[CH:4]/[C:3]1[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 678472-Chloro-6-fluorobenzaldehyde

Product 1

HCID 5709173HCID 5709173, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(72) To a solution of the 2-chloro-6-fluoro-benzaldehyde (1.59 g, 10.0 mmol) and acetone (290 mg, 5.00 mmol) in 15 ml of ethanol was added 5 ml of 40% potassium hydroxide at 10° C. After stirring for several hours at room temperature, the solution was filtered. The precipitate was recrystallized from ethanol to afford 879 mg (51.7%) of a light-yellow powder: mp 143.5-144.3° C. 1H NMR (250 MHz) δ 7.98-7.91 (d, 2 H), 7.36-7.22 (m, 6 H), 7.13-7.03 (m, 2 H); 13C NMR (62.7 MHz) 189.6, 134.0, 132.1, 131.8, 131.2, 131.0, 126.3, 115.4, 115.0 ppm. Elemental Analysis. Calculated for C17 H10Cl2F2O5: C, 60.20; H, 2.98. Found: C, 60.07; H, 2.99.

Workup

  1. filtrationthe solution was filtered
  2. customThe precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-5bee017a4cc049c4ad704cb0d01c6abf
Source dataset
uspto-grants-2008_10
Patent number
US07432303B2

Reaction notes

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