Hexamethylenetetramine → HCID 21919188, compound

HRID 1830213Notes

Reaction equation

HRID 1830213 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][CH:10]=[CH:9][C:8]=1[OH:13].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[C:8]([OH:13])=[C:9]([CH:10]=[CH:11][CH:12]=1)[CH:36]=[O:37]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 219191522-(3,4,5,6-Tetramethoxy-2-methylbenzyl)phenol

Product 1

HCID 21919188HCID 21919188, compoundYield 27%

Conditions

Temperature
80 °C

Procedure

2-(3,4,5,6-Tetramethoxy-2-methylbenzyl)phenol (8.64 g, 27.17 mmol) and hexamethylenetetramine (5.00 g, 35.67 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 (2.50 g, 7.23 mmol, 27%).

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-dd30e19c2c954e98a9878fb60b997825
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

Loading…