Acetone → HCID 10270588, compound

HRID 990904Notes

Reaction equation

HRID 990904 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+]>>[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

4

Reactant 3

HCID 180AcetoneHCID 67372,6-DichlorobenzaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 10270588HCID 10270588, compound

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 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, 2H), 7.40-7.36 (d, 4H), 7.26-7.19 (d, 2H), 7.24-7.18 (m, 2H); 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-a04b7ac4d5af4d469cf7e3725455c812
Source dataset
uspto-grants-2002_10
Patent number
US06462075B1

Reaction notes

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