Water → 6-Methyl-2H-1,3-benzodioxole-5-carbaldehyde

HRID 1835404Notes

Reaction equation

HRID 1835404 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].BrC1[CH:12]=[C:11]2[O:13][CH2:14][O:15][C:10]2=CC=1C.CN(C)[CH:19]=[O:20].O>O1CCCC1>[CH3:4][C:3]1[CH:12]=[C:11]2[O:13][CH2:14][O:15][C:10]2=[CH:1][C:2]=1[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 787285-Bromo-6-methyl-1,3-benzodioxoleHCID 178418339Butyllithium

Product 1

HCID 31462426-Methyl-2H-1,3-benzodioxole-5-carbaldehydeYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13 ml (20 mmol) of n-butyllithium (1.5 M hexane solution) was dropwise added at −78° C. to a solution having 4.0 g (19 mmol) of 2-bromo-4,5-(methylenedioxy)toluene dissolved in 50 ml of tetrahydrofuran, followed by stirring for 30 minutes, and 1.5 ml (19 mmol) of dimethylformamide was added thereto, followed by stirring for 70 minutes. 30 ml of water was added to the mixture to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. Extraction with chloroform was carried out, the organic layer was dried over anhydrous sodium sulfate and subjected to filtration by using a silica gel cake, and the solvent was distilled off under reduced pressure to obtain 3.1 g (yield 99%) of 2-methyl-4,5-(methylenedioxy)benzaldehyde (m.p. 84-86° C.).

Workup

  1. stirringby stirring for 70 minutes
  2. customto terminate
  3. customthe reaction, and tetrahydrofuran
  4. distillationwas distilled off under reduced pressure
  5. extractionExtraction with chloroform
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0b0e790af22741de871938c648ce9674
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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