Thioanisole → Ibuprofenal

HRID 652310Notes

Reaction equation

HRID 652310 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-].C1(SC)C=CC=CC=1>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

5

Reactant 3

HCID 7520ThioanisoleHCID 5360315Magnesium ChlorideHCID 10330171Oxirane, 2-methyl-2-[4-(2-methylpropyl)phenyl]-

Product 1

HCID 595156IbuprofenalYield 98.5%

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 3.43 g (0.036 mole) of anhydrous powdered (100 mesh, Tyler) magnesium chloride and 5.0 g (0.04 mole) of thioanisole and the mixture was stirred for 10 hours at room temperature. The reaction mixture was washed with dilute hydrochloric acid and then with aqueous sodium chloride several times until neutral, and subjected to distillation under atmospheric pressure to remove dichloromethane. The resulted residue was distilled under reduced pressure to afford 37.4 g of 2-(4-isobutylphenyl)propionaldehyde as colorless oil distilled at 127°-130° C. (8 mmHg). The yield is 98.5%

Workup

  1. washThe reaction mixture was washed with dilute hydrochloric acid
  2. distillationwith aqueous sodium chloride several times until neutral, and subjected to distillation under atmospheric pressure
  3. customto remove dichloromethane
  4. distillationThe resulted residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-c3a2f67710454074a50228111f505441
Source dataset
uspto-grants-1987_06
Patent number
US04670607

Reaction notes

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