Dimethylformamide → HCID 22222788, compound

HRID 2231856Notes

Reaction equation

HRID 2231856 reaction equation
[CH2:1]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Mg].CN(C)[CH:20]=[O:21].[Cl-].[NH4+]>O1CCCC1.C(Cl)(Cl)(Cl)Cl>[CH2:1]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:20]=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 21924050HCID 21924050, compound2×

Product 1

HCID 22222788HCID 22222788, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent4×

Procedure

A third of a solution of 22 g of 2-nonylbromobenzene in 35 ml of tetrahydrofuran is added to a mixture, stirred under an argon atmosphere, of 3.4 g of magnesium chips, 25 ml of tetrahydrofuran and 3 drops of carbon tetrachloride and the whole is heated at the boil under reflux for 30 minutes. The remainder of the 2-nonylbromobenzene solution is then added dropwise over a period of one hour and the reaction mixture is maintained under reflux for 2 hours. After dilution with 40 ml of tetrahydrofuran the whole is cooled in an ice bath to approximately 5° and a solution of 11.6 ml of dimethylformamide in 20 ml of tetrahydrofuran is added dropwise over a period of 15 minutes. After stirring for one hour at room temperature, 250 ml of saturated ammonium chloride solution are added to the reaction mixture, the organic layer is separated off and the aqueous layer is extracted three times with ether. The residue that remains after the combined ethereal extracts have been dried and concentrated by evaporation is purified by chromatography on silica gel with mixtures of petroleum ether with an increasing amount of methylene chloride, yielding the desired 2-nonylbenzaldehyde in the form of a pale yellow liquid.

Workup

  1. temperaturethe whole is heated at the boil
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe reaction mixture is maintained
  4. temperatureunder reflux for 2 hours
  5. customthe organic layer is separated off
  6. extractionthe aqueous layer is extracted three times with ether
  7. customhave been dried
  8. concentrationconcentrated by evaporation
  9. customis purified by chromatography on silica gel with mixtures of petroleum ether with an increasing amount of methylene chloride

Sources & evidence

ORD record
ord-aadfea8341704d63b1f6e3edff28de42
Source dataset
uspto-grants-1988_11
Patent number
US04785004

Reaction notes

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