2-Nitropropane → 3-Methoxy-5-methylbenzaldehyde

HRID 1016782Notes

Reaction equation

HRID 1016782 reaction equation
[N+](C(C)C)([O-])=[O:2].Br[CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([O:16][CH3:17])[CH:10]=1.CC[O-].[Na+]>CCO>[CH3:17][O:16][C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([CH3:15])[CH:12]=1)[CH:8]=[O:2]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 5855341-(Bromomethyl)-3-methoxy-5-methylbenzeneHCID 2723922Sodium ethoxide

Product 1

HCID 110947973-Methoxy-5-methylbenzaldehydeYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitropropane (6.77 ml, 71.3 mmol) and subsequently 1-bromomethyl-3-methoxy-5-methyl-benzene (14.6 g, 67.9 mmol) were added to a solution of NaOEt (4.72 g, 67.9 mmol) in EtOH (60 ml). The mixture was heated for 1.5 h. to 65° C. After cooling the colorless precipitate of filtered off and the filtrate was concentrated. The product was purified by chromatography (SiO2, CH2Cl2/hexane 1:2). There were obtained 7.87 g (77%) of 3-methoxy-5-methyl-benzaldehyde as a colorless liquid.

Workup

  1. temperatureThe mixture was heated for 1.5 h. to 65° C
  2. temperatureAfter cooling the colorless precipitate
  3. filtrationof filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe product was purified by chromatography (SiO2, CH2Cl2/hexane 1:2)

Sources & evidence

ORD record
ord-3935187490dd478bae9d6afdb94e9375
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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