Dimethylformamide → 2-Isopropyl-6-methylbenzaldehyde

HRID 427510Notes

Reaction equation

HRID 427510 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([CH3:11])[CH3:10].[Mg].CN(C)[CH:15]=[O:16]>C(OCC)C>[CH:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH:15]=[O:16])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 5462224MagnesiumHCID 145345702-Bromo-1-isopropyl-3-methylbenzene

Product 1

HCID 124670472-Isopropyl-6-methylbenzaldehydeYield 33%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-bromo-2-isopropyl-6-methylbenzene (6.9 g, 32.4 mmol) in diethyl ether (50 ml) was added magnesium turnings (0.9 g, 37 mmol) and the mixture was refluxed in nitrogen atmosphere until the reaction was started and was then stirred overnight at room temperature. Dimethylformamide (4 ml) was added dropwise during 10 min. and the mixture was stirred for 30 min. Saturated ammmoniumchloride solution (30 ml) was added and the mixture was stirred for 1 h. The organic layer was separated, filtrated and evaporated under reduced pressure. Purification by column chromatography on silica gel using hexane:methylene chloride (3:2) as eluent gave 1.75 g (33%) of the title compound .

Workup

  1. temperaturethe mixture was refluxed in nitrogen atmosphere until the reaction
  2. stirringthe mixture was stirred for 30 min
  3. stirringthe mixture was stirred for 1 h
  4. customThe organic layer was separated
  5. filtrationfiltrated
  6. customevaporated under reduced pressure
  7. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-bb5ea198fbde4afeb2dd934f21b8792d
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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