Hexamethylenetetramine → HCID 19858062, compound

HRID 2073387Notes

Reaction equation

HRID 2073387 reaction equation
[CH3:1][C:2]1([CH3:17])[C:6](=[O:7])[O:5][C:4]2[CH:8]=[CH:9][C:10]3[C:15]([C:3]1=2)=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3.FC(F)(F)[C:20](O)=[O:21].C1N2CN3CN(C2)CN1C3>>[CH:20]([C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][C:13]=1[CH3:16])[C:3]1[C:2]([CH3:17])([CH3:1])[C:6](=[O:7])[O:5][C:4]=1[CH:8]=[CH:9]2)=[O:21]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 19858068HCID 19858068, compound

Product 1

HCID 19858062HCID 19858062, compound

Procedure

A mixture of 1,1,8-trimethyl-2-(1H)-naphtho[2,1-b]furanone (3.85)g, trifluoracetic acid (25 ml) and hexamine (3.5 g) was stirred under reflux for 18 h. The bulk of the trifluoroacetic acid was evaporated under reduced pressure and the residue was treated with water and heated at 90° for 10 minutes. The mixture was neutralised with potassium hydrogen carbonate and extracted twice with chloroform. The combined extracts were dried and evaporated to dryness, and the residue was recrystallised from ethyl acetate to give 7-formyl-1,1,8-trimethyl-2(1H)-naphtho[2,1-b]furanone (2.2 g), m.p. 193°-195° C.

Workup

  1. temperatureunder reflux for 18 h
  2. customThe bulk of the trifluoroacetic acid was evaporated under reduced pressure
  3. additionthe residue was treated with water
  4. temperatureheated at 90° for 10 minutes
  5. extractionextracted twice with chloroform
  6. customThe combined extracts were dried
  7. customevaporated to dryness
  8. customthe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-37837a46ffaf41399e01530dd358d1aa
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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