Hexamethylenetetramine → 4-(2-Methylbutan-2-yl)benzaldehyde

HRID 1610714Notes

Reaction equation

HRID 1610714 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:24](O)=[O:25]>>[C:1]([C:6]1[CH:7]=[CH:8][C:9]([CH:24]=[O:25])=[CH:10][CH:11]=1)([CH2:4][CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 16295tert-Amylbenzene

Product 1

HCID 4737804-(2-Methylbutan-2-yl)benzaldehyde

Procedure

A solution of tert-pentylbenzene (10.04 g, 67.72 mmol) and hexamethylenetetramine (9.49 g, 67.7 mmol) in trifluoroacetic acid (100 ml) was stirred at 90° C. overnight. The reaction solution was evaporated under reduced pressure, diluted with water, alkalified with potassium carbonate, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude product of 4-(tert-pentyl)benzaldehyde as a dark brown liquid.

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fd2cdb48d5be4c41aa057d04edf96aec
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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