Magnesium Chloride → Ibuprofenal

HRID 652311Notes

Reaction equation

HRID 652311 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([CH3:14])[O:13][CH2:12]2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[Cl-].[Mg+2].[Cl-]>ClCCl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:14])[CH:12]=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 5360315Magnesium ChlorideHCID 10330171Oxirane, 2-methyl-2-[4-(2-methylpropyl)phenyl]-

Product 1

HCID 595156IbuprofenalYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 38.0 g (0.2 mole) of 2-(4-isobutylphenyl)-1,2-epoxypropane in 130 ml of dichloromethane was added 2.67 g (0.028 mole) of anhydrous powdered (100 mesh, Tyler) magnesium chloride and 5.0 g (0.04 mole) of thionisole, and the mixture was refluxed with stirring for 3 hours. After cooling the reaction mixture, insoluble materials were filtered off and washed with small amount of dichloromethane and the washings were combined with the filtrate. The combined solution was washed with aqueous sodium chloride and subjected to distillation under atmospheric pressure to remove dichloromethane. The remaining residue was subjected to distillation under reduced pressure to obtain 36.8 g of 2-(4-isobutylphenyl)propionaldehyde distilled at 127°-129° C. (8 mmHg) as colorless oil. Yield; 96.8%, purity; above 99%.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter cooling the reaction mixture, insoluble materials
  3. filtrationwere filtered off
  4. washwashed with small amount of dichloromethane
  5. washThe combined solution was washed with aqueous sodium chloride
  6. distillationsubjected to distillation under atmospheric pressure
  7. customto remove dichloromethane
  8. distillationThe remaining residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-0fa3ea1185f649758ea9e382ff35020a
Source dataset
uspto-grants-1987_06
Patent number
US04670607

Reaction notes

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