Hydrochloric Acid → Phenethyl isocyanate

HRID 848200Notes

Reaction equation

HRID 848200 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[C:11](Cl)(Cl)=[O:12]>C1(C)C=CC=CC=1>[C:3]1([CH2:2][CH2:1][N:9]=[C:11]=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 6371Phosgene2×

Product 1

HCID 160602Phenethyl isocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

40 grams of phenethyl amine in 300 ml of dry toluene saturated with dry HCl gas was mixed until a heavy white precipitate formed. An additional 200 ml of dry toluene was added with 50 ml of phosgene (12.5% in benzene). The mixture was refluxed (10 min.) and then 450 ml of phosgene was slowly added over 30 minutes and the mixture refluxed for 4 hours. The reaction mixture was allowed to cool to room temperature slowly and the solvent removed in vacuo leaving a yellow oil. Vacuum distillation of the oil at 82° to 83° C./0.1 mm yielded 1.8 g of end product.

Workup

  1. customformed
  2. temperatureThe mixture was refluxed (10 min.)
  3. temperaturethe mixture refluxed for 4 hours
  4. customthe solvent removed in vacuo
  5. customleaving a yellow oil
  6. distillationVacuum distillation of the oil at 82° to 83° C./0.1 mm
  7. customyielded 1.8 g of end product

Sources & evidence

ORD record
ord-2aca5d3d3fd64db096f5efcbbbeed1af
Source dataset
uspto-grants-1981_10
Patent number
US04294925

Reaction notes

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