Pinacolone → 5-(4-Chlorophenyl)-2,2-dimethylpent-4-en-3-one

HRID 1389002

Reaction equation

HRID 1389002 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6416PinacoloneHCID 77264-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 3060495-(4-Chlorophenyl)-2,2-dimethylpent-4-en-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chlorobenzaldehyde (140.5 g) and pinacolone (100 g) in industrial methylated spirit (IMS; 200 ml) were added dropwise over 25 minutes to sodium hydroxide (40 g) in water (70 ml) and IMS (150 ml) with external cooling (ice/water) applied to maintain a temperature of not more than 25°. The resulting creamy suspension was stirred for a further 3 hours at 18° and was then filtered. The residue was washed with aqueous IMS and dried to give 4-chlorobenzal pinacolone, m.p. 83°-84°. The filtrate was concentrated under reduced pressure and allowed to stand for 2 days to give more of the chalcone product, m.p. 83°-84°.

Workup

  1. temperatureto maintain a temperature of not more than 25°
  2. filtrationwas then filtered
  3. washThe residue was washed with aqueous IMS
  4. customdried

Sources & evidence

ORD record
ord-8eed1b590bd94410a7a223ad9011a7a4
Source dataset
uspto-grants-1981_01
Patent number
US04243405

Linked notes

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