Water → 1-Chloro-2-[(1E)-prop-1-en-1-yl]benzene

HRID 574069Notes

Reaction equation

HRID 574069 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=O.[CH3:10][CH2:11]C(=O)CC.B(F)(F)F.CCOCC.O>CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:10]/[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 69962-ChlorobenzaldehydeHCID 7288Ethyl ketoneHCID 8000Boron trifluoride etherate

Product 1

HCID 144196771-Chloro-2-[(1E)-prop-1-en-1-yl]benzeneYield 59.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

48 ml of 2-chlorobenzenaldehyde (0.42 mol) and 49.7 ml of 3-pentanone (0.47 mol) were dissolved in 600 mL of hexane in flask, and then stirred with raising the temperature. 53.6 ml of Boron trifluoride etherate (BF3OEt2, 0.42 mol) was added to the resultant under reflux conditions. When the reaction was completed, water was added thereto. After layer separation, the obtained organic layer was washed twice with 1M sodium hydroxide solution (1M NaOH), and then the separated organic layer was washed with water. The separated organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4) and concentrated. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (38 g, yield 58%).

Workup

  1. temperaturewith raising the temperature
  2. customAfter layer separation
  3. washthe obtained organic layer was washed twice with 1M sodium hydroxide solution (1M NaOH)
  4. washthe separated organic layer was washed with water
  5. concentrationconcentrated
  6. customThe concentrated residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-780a0ead4e3546dda39cb1f93420f692
Source dataset
uspto-grants-2015_05
Patent number
US09034848B2

Reaction notes

Loading…