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

HRID 537383Notes

Reaction equation

HRID 537383 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%). 1H NMR (400 MHz, CDCl3) δ1.94 (d, J=4.8 Hz, 3H), 6.24 (m, 1H), 6.78 (d, J=14 Hz, 1H), 7.11˜7.51 (m, 4H)

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-6da739ff5af1461286a9065e89f4ca77
Source dataset
uspto-grants-2014_10
Patent number
US08859817B2

Reaction notes

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