Hexamethylenetetramine → HCID 21919177, compound

HRID 1830212Notes

Reaction equation

HRID 1830212 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) and the solution was stirred under heating at 80° C. for 4 hours. After the completion of reaction, the solvent was removed by distillation and to the obtained residue, water (100 ml) was added. The resulting solution was stirred for 30 minutes and extracted with methylene chloride. The extract was washed with water and then dried, the solvent was removed by distillation and the obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=4:1) to obtain the titled compound (12.20 g, 35.26 mmol, 78%).

Workup

  1. customAfter the completion of reaction
  2. customthe solvent was removed by distillation and to the obtained residue, water (100 ml)
  3. additionwas added
  4. stirringThe resulting solution was stirred for 30 minutes
  5. extractionextracted with methylene chloride
  6. washThe extract was washed with water
  7. customdried
  8. customthe solvent was removed by distillation
  9. customthe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1a43647061c64613b1e89bb84b48d3dd
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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