Acetone → HCID 10270588, compound

HRID 2113936Notes

Reaction equation

HRID 2113936 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl: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]([Cl:10])[C:3]=1/[CH:4]=[CH:11]/[C:12](=[O:13])/[CH:14]=[CH:4]/[C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10]

Participants

5

Reactant 3

HCID 180AcetoneHCID 67372,6-DichlorobenzaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 10270588HCID 10270588, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(73) To a 0.33 M solution of 2,6-dichlorobenzaldehyde (1.75 g, 10 mmol) and acetone (290 mg, 5 mmol) in 30 ml of ethanol was added 5 ml of 40% potassium hydroxide at 10° C. After stirring for 18 hr at room temperature, a solid precipitated and was filtered. The precipitate was recrystallized from ethanol to afford 1.46 g (78.5%) of pale yellow, cotton-like flakes: mp 154.0-154.4° C. (lit. mp 145-146° C., Unterhalt, Arch. Pharm., 1978, 311, 262-267). 1H NMR (250 MHz) δ 7.85-7.79 (d, 2 H), 7.40-7.36 (d, 4 H), 7.26-7.19 (d, 2 H), 7.24-7.18 (m, 2 H); 13C NMR (62.7 MHz) 189.1, 137.6, 135.4, 133.3, 132.5, 130.2, 129.1 ppm.

Workup

  1. customa solid precipitated
  2. filtrationwas filtered
  3. customThe precipitate was recrystallized from ethanol
  4. customto afford 1.46 g (78.5%) of pale yellow, cotton-like flakes

Sources & evidence

ORD record
ord-e8a5b52be6b84988a99ac1faaff3901a
Source dataset
uspto-grants-2008_10
Patent number
US07432303B2

Reaction notes

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