Acetone → HCID 18371119, compound

HRID 380936Notes

Reaction equation

HRID 380936 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=O.[OH-].[Na+].[CH3:13][C:14]([CH3:16])=[O:15]>O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1/[CH:4]=[CH:13]/[C:14](=[O:15])[CH3:16]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 1362842,6-Difluorobenzaldehyde

Product 1

HCID 18371119HCID 18371119, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100ml reaction bottle equipped with magnetic stir bar was charged 5.0 g (35.2 mmole) of 2,6-difluorobenzaldehyde in 20 ml acetone and to this was added 3.4 g of 50% aqueous NaOH (42 mmole) in 60 ml water (exothermic) and stirred at room temperature. The reaction was monitored by GLC and after 2 hours the reaction was worked up. The reaction mixture was extracted with 50 ml CHCl3, washed with 50 ml H2O, dried over anhydrous MgSO4, filtered, and the solvent removed in vacuuo on a rotary evaporator to afford 5.7 g of trans-4-(2,6-difluorophenyl)-3-buten-2-one as a yellow oil in 81% purity by GC. and 89.5% isolated yield.

Workup

  1. customTo a 100ml reaction bottle
  2. customequipped with magnetic stir bar
  3. extractionThe reaction mixture was extracted with 50 ml CHCl3
  4. washwashed with 50 ml H2O
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuuo on a rotary evaporator

Sources & evidence

ORD record
ord-0be8bacc173e47b2af042695473ec242
Source dataset
uspto-grants-2001_10
Patent number
US06303818B1

Reaction notes

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