Hexamethylenetetramine → 4-Hydroxy-3-methoxy-5-(trifluoromethyl)benzaldehyde

HRID 1974725Notes

Reaction equation

HRID 1974725 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[C:4]=1[OH:13].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:26](O)=[O:27]>>[OH:13][C:4]1[C:5]([C:9]([F:11])([F:10])[F:12])=[CH:6][C:7]([CH:26]=[O:27])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 151333362-Methoxy-6-(trifluoromethyl)phenol

Product 1

HCID 193891994-Hydroxy-3-methoxy-5-(trifluoromethyl)benzaldehyde

Procedure

A solution containing 1.9 g of 2-methoxy-6-trifluoromethylphenol and 1.4 g of hexamethylenetetramine in 20 ml of trifluoroacetic acid was refluxed for 1 h. The solvent was removed in reduced pressure, 50 ml of 1N hydrochloric acid was added to the residue and the solution was extracted with dichloromethane. Most part of the solvent was evaporated in vacuo and petroleum ether was added, whereupon the product crystallized. Yield 0.7 g (32%), m.p. 151°-152° C.

Workup

  1. temperaturewas refluxed for 1 h
  2. customThe solvent was removed in reduced pressure, 50 ml of 1N hydrochloric acid
  3. additionwas added to the residue
  4. extractionthe solution was extracted with dichloromethane
  5. customMost part of the solvent was evaporated in vacuo and petroleum ether
  6. additionwas added, whereupon the product
  7. customcrystallized

Sources & evidence

ORD record
ord-6fad3a806ac4465ea6ca454c67c15448
Source dataset
uspto-grants-1994_02
Patent number
US05283352

Reaction notes

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