Water → 3-(3-Chlorophenyl)propionaldehyde

HRID 843573Notes

Reaction equation

HRID 843573 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

HCID 962WaterHCID 6344DichloromethaneHCID 14905m-Chlorostyrene

Product 1

HCID 104195793-(3-Chlorophenyl)propionaldehyde

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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

  1. customReaction
  2. additionwas completed within 30 minutes of the addition
  3. extractionextracted with ether (3×)
  4. washthe combined organic layers were washed with saturated NaHCO3 solution, water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to a volume of about 15 mL
  7. 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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