Hexamethylenetetramine → (+)-4(-2-Methylbutyl)benzaldehyde

HRID 1981452Notes

Reaction equation

HRID 1981452 reaction equation
C1N2CN3CN(C2)CN1C3.[CH3:11][CH:12]([CH2:20][CH3:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.FC(F)(F)[C:24](O)=[O:25]>>[CH3:11][CH:12]([CH2:20][CH3:21])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:24]=[O:25])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 107203(2-Methylbutyl)benzene

Product 1

HCID 20398737(+)-4(-2-Methylbutyl)benzaldehyde

Procedure

Trifluoroacetic acid (150 cc) was added to a flask containing 14.0 gm hexamethylenetetramine (HMTA). (+)2-methylbutylbenzene (14.8 gm) was then added and the mixture was refluxed for 21 hours. The deep orange mixture was distilled to remove excess trifluoroacetic acid. When about one third the volume remained, the mixture was poured into 600 ml ice water and stirred for 15 minutes. Sodium carbonate was added with stirring until the mixture was basic and the product was extracted with ether. The ether extract was washed with water and dried over sodium sulfate. The ether was removed leaving 18 gm crude (+)-4(-2-methylbutyl)benzaldehyde. This was vacuum distilled (78° C. at 0.07 mm Hg). The structure of the product was confirmed by NMR. The yield of the product was 78%.

Workup

  1. temperaturethe mixture was refluxed for 21 hours
  2. distillationThe deep orange mixture was distilled
  3. customto remove excess trifluoroacetic acid
  4. additionthe mixture was poured into 600 ml ice water
  5. additionSodium carbonate was added
  6. stirringwith stirring until the mixture
  7. extractionthe product was extracted with ether
  8. extractionThe ether extract
  9. washwas washed with water
  10. dry with materialdried over sodium sulfate
  11. customThe ether was removed

Sources & evidence

ORD record
ord-ac9d0af6923e447bb83f6ed1cc551172
Source dataset
uspto-grants-1985_04
Patent number
US04514045

Reaction notes

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