Sodium Methoxide → 2-(4-Iodophenyl)propionaldehyde dimethyl acetal

HRID 904235Notes

Reaction equation

HRID 904235 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[CH:9]=[O:10])=[CH:4][CH:3]=1.[CH:12]([O-])([O-])[O:13]C.[CH3:17][O-].[Na+]>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:17][O:10][CH:9]([O:13][CH3:12])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=1)[CH3:11]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 233338292-(4-Iodophenyl)propanalHCID 53629101Methylorthoformate

Product 1

HCID 233338172-(4-Iodophenyl)propionaldehyde dimethyl acetalYield 762.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 39.2 g of 2-(4-iodophenyl)propionaldehyde in 39.2 ml of methanol was added 0.2 g of p-toluenesulfonic acid, and the mixture was stirred for 10 minutes. After addition of 19.2 g of methyl orthoformate, stirring was continued for 30 minutes. After completion of the reaction, 1.0 g of sodium methylate was added to the reaction mixture and the solvent was removed by distillation under reduced pressure. On distillation of the residue, there was obtained 43.2 g of 2-(4-iodophenyl)propionaldehyde dimethyl acetal, b.p. 155°-160° C./15 mmHg.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes
  3. additionwas added to the reaction mixture
  4. customthe solvent was removed by distillation under reduced pressure
  5. distillationOn distillation of the residue

Sources & evidence

ORD record
ord-caeaf1a25eab48fcbfeb10d9051bf2f6
Source dataset
uspto-grants-1980_10
Patent number
US04230719

Reaction notes

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