Acetone → 4-(5-Chloro-2-methoxyphenyl)-3-buten-2-one

HRID 1700711Notes

Reaction equation

HRID 1700711 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:12][CH3:13])=[C:8]([CH:11]=1)[CH:9]=O.[CH3:14][C:15]([CH3:17])=[O:16]>O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:12][CH3:13])=[C:8]([CH:9]=[CH:14][C:15](=[O:16])[CH3:17])[CH:11]=1

Participants

5

Reactant 3

HCID 180Acetone2×HCID 14798Sodium HydroxideHCID 37183565-Chloro-2-methoxybenzaldehyde

Product 1

HCID 536609684-(5-Chloro-2-methoxyphenyl)-3-buten-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In water (100 ml) was dissolved sodium hydroxide (3.0 g), and to the solution was added acetone (80 ml) and then was added dropwise a solution of 5-chloro-2-methoxybenzaldehyde (11.8 g) in acetone (30 ml). The reaction solution was stirred at room temperature for 2 hours, and acetone was evaporated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and concentrated under reduced pressure. The residue was purified with silica gel column chromatography to give 4-(5-chloro-2-methoxyphenyl)-3-buten-2-one (6.8 g).

Workup

  1. customacetone was evaporated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-ab7cdc2fdce54d36b9569af9c2294b54
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

Loading…