Sodium Hydroxide → 4-Ethylthiophene-2-carbaldehyde

HRID 634842Notes

Reaction equation

HRID 634842 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[CH3:7].[C:13]([O-])(O)=[O:14].[Na+].[OH-].[Na+]>ClCCl.CN(C=O)C>[CH2:6]([C:8]1[CH:12]=[C:11]([CH:13]=[O:14])[S:10][CH:9]=1)[CH3:7]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 745303-EthylthiopheneHCID 516892Sodium Bicarbonate

Product 1

HCID 152096224-Ethylthiophene-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

31.5 ml of phosphorus oxychloride was added dropwise to 26.0 ml of DMF and stirring carried out for 1 hour. 25.0 g (223 mmol) of 3-ethylthiophene was added dropwise thereto and, after stirring for 1 hour, stirring was conducted at 100° C. for 1 hour. After cooling to room temperature, dilution was carried out with dichloromethane and the mixture poured into saturated bicarbonate of soda solution and neutralization performed with aqueous sodium hydroxide solution. Extraction was then carried out with dichloromethane, followed by drying and concentrating. The residue was distilled and 25.7 g (183 mmol, 0.1 mmHg, 48-49° C). of an approximately 3:1 mixture of 3-ethylthiophenealdehyde and 4-ethylthiophenealdehyde was obtained as a colourless liquid.

Workup

  1. stirringafter stirring for 1 hour
  2. stirringstirring
  3. waitwas conducted at 100° C. for 1 hour
  4. extractionExtraction
  5. customby drying
  6. concentrationconcentrating
  7. distillationThe residue was distilled
  8. custom25.7 g (183 mmol, 0.1 mmHg, 48-49° C)
  9. additionof an approximately 3:1 mixture of 3-ethylthiophenealdehyde

Sources & evidence

ORD record
ord-124f8bc437734d3ab2b2b8185c4fb3d6
Source dataset
uspto-grants-2001_02
Patent number
US06184245B2

Reaction notes

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