2,4,6-Trimethylaniline → 4-amino-3,5-dimethylbenzaldehyde

HRID 1665914Notes

Reaction equation

HRID 1665914 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].[O:11]1CCOCC1>>[NH2:4][C:3]1[C:5]([CH3:10])=[CH:6][C:7]([CH:9]=[O:11])=[CH:8][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 312751,4-Dioxane

Product 1

HCID 100347774-amino-3,5-dimethylbenzaldehydeYield 15.2%

Procedure

To a solution of 2,4,6-trimethylaniline (29.8 g, 0.22 mol) in dioxane (300 mL) DDQ (49.9 g, 0.22 mol) is added. The brown suspension is stirred at rt for 18 h before it is filtered. The solvent of the filtrate is evaporated and the crude product is purified by CC on silica gel eluting with hexane:EA 1:1 to give 4-amino-3,5-dimethyl-benzaldehyde (5.0 g) as a beige solid; LC-MS: tR=0.78 min, [M+1]+=150.26.

Workup

  1. filtrationis filtered
  2. customThe solvent of the filtrate is evaporated
  3. customthe crude product is purified by CC on silica gel eluting with hexane:EA 1:1

Sources & evidence

ORD record
ord-315e99e5b3704f0ab8b85010a914f31d
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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