Water → 3-(3-Chlorophenyl)propionaldehyde
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH2:6].[CH2:10](Cl)Cl.[OH2:13]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][CH2:6][CH:10]=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 25° C. solution of 3-chlorostyrene in anhydrous CH2Cl2 ( 10.0 g, 72.15 mmol) was added a well-stirred solution of Pb(OAc)4 (35.2 g, 79.4 mmol) in trifluoroacetic acid (150 mL), dropwise. Reaction was completed within 30 minutes of the addition and after being stirred for a further 30 minutes, the mixture was poured into water, extracted with ether (3×), the combined organic layers were washed with saturated NaHCO3 solution, water, dried (MgSO4), and concentrated to a volume of about 15 mL and immediately used for the following reaction described below.
Workup
- customReaction
- additionwas completed within 30 minutes of the addition
- extractionextracted with ether (3×)
- washthe combined organic layers were washed with saturated NaHCO3 solution, water
- dry with materialdried (MgSO4)
- concentrationconcentrated to a volume of about 15 mL
- customimmediately used for the following reaction
Sources & evidence
- ORD record
- ord-80ae57e962354b54b94b849c380ee04b
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380178B1
Reaction notes
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