Ammonium thiocyanate → (4-Ethenylphenyl)methyl thiocyanate

HRID 1744995

Reaction equation

HRID 1744995 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[CH:5]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Cl)=[CH:9][CH:8]=1)=[CH2:6]>CC(C)=O>[CH:5]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11][S:1][C:2]#[N:3])=[CH:9][CH:8]=1)=[CH2:6]

Participants

4

Reactant 2

HCID 15666Ammonium thiocyanateHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 15217596(4-Ethenylphenyl)methyl thiocyanateYield 59.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ammonium thiocyanate (2 equiv., 43 g, 0.50 mol) was dissolved in acetone (200 ml) and 4-vinylbenzyl chloride (43 g, 0.25 mol) was added to the reaction flask. The mixture was stirred at room temperature overnight. The reaction mixture was filtered and acetone removed under reduced pressure. The resulting product was dissolved in hexane, filtered, and the solvent removed under reduced pressure. The monomer was isolated as a red-orange, slightly viscous liquid (26 g, yield 52%). 1H NMR (CDCl3) δ (ppm) 4.13 (s, 2H), 5.29 (d, 1H), 5.76 (d, 1H), 6.67 (dd, 1H), 7.31 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customacetone removed under reduced pressure
  3. dissolutionThe resulting product was dissolved in hexane
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c9b4b21ea8d046b6b4d21f6947bfff17
Source dataset
uspto-grants-2006_03
Patent number
US07019096B2

Linked notes

Loading…