Ethanol → HCID 10855492, compound

HRID 247563Notes

Reaction equation

HRID 247563 reaction equation
C1N2CN3CN(C2)CN1C3.[I-].[Na+].Cl[CH2:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:17]2[CH2:18][CH2:19][C:16]=12.C([OH:25])C>O>[CH:14]([C:15]1[CH:22]=[CH:21][CH:20]=[C:17]2[CH2:18][CH2:19][C:16]=12)=[O:25]

Participants

6

Reactant 4

HCID 702EthanolHCID 4101HexamethylenetetramineHCID 5238Sodium IodideHCID 126177184-Chloromethylbenzocyclobutene

Product 1

HCID 10855492HCID 10855492, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a hot solution of hexamethylene tetramine (14 g) and sodium iodide (16 g) in 140 g of ethanol was added 4-chloromethylbenzocyclobutene (15.2 g) with stirring. After standing at ambient temperature for 2-3 h, the mixture was diluted with 150 ml of water and then heated at reflux for 2 h. The resulting mixture was steam distilled and the distillate was extracted three times with ether. The combined ether extract was washed with water, dried over magnesium sulfate, and fractionally distilled to give 4-formylbenzocyclobutene: 1H NMR (CDCl3) δ 3.17 (s, 4), 7.15 (d, 1), 7.51 (s, 1), 7.67 (d, 1) and 9.86 ppm (s, 1).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. distillationdistilled
  4. extractionthe distillate was extracted three times with ether
  5. extractionThe combined ether extract
  6. washwas washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationfractionally distilled

Sources & evidence

ORD record
ord-c886025b78ac41a8b5096a4aeff1a95b
Source dataset
uspto-grants-1987_11
Patent number
US04708990

Reaction notes

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