Hexamethylenetetramine → HCID 21919177, compound

HRID 1245151Notes

Reaction equation

HRID 1245151 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:23])=[C:5]([C:14]([O:21][CH3:22])=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:36](O)=[O:37]>>[CH3:1][O:2][C:3]1[C:4]([CH3:23])=[C:5]([C:14]([O:21][CH3:22])=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH:8]=1)[CH:36]=[O:37]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 21919208HCID 21919208, compound

Product 1

HCID 21919177HCID 21919177, compoundYield 78%

Conditions

Temperature
80 °C

Procedure

4-(3,4,5,6-Tetramethoxy-2-methylbenzyl)phenol (14.5 g, 45.60 mmol) and hexamethylenetetramine (8.30 g, 59.29 mmol) were dissolved in trifluoroacetic acid (100 ml) followed by heating at 80° C. with stirring for 4 hours. After completion of the reaction, the solvent was evaporated therefrom, water (100 ml) was added to the resulting residue and the mixture was stirred for 30 minutes and extracted with methylene chloride. The extract was washed with water and dried, the solvent was evaporated therefrom and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (12.20 g, 35.26 mmol, 78%).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionwater (100 ml) was added to the resulting residue
  4. stirringthe mixture was stirred for 30 minutes
  5. extractionextracted with methylene chloride
  6. washThe extract was washed with water
  7. customdried
  8. customthe solvent was evaporated
  9. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-8a7ac032b89440488529c41b7e54e109
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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