Formamide → 2-Phenyl-1-propanol

HRID 1447098Notes

Reaction equation

HRID 1447098 reaction equation
[C:1]1([CH:7]([CH3:10])[CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1CCCCC1>O>[C:1]1([CH:7]([CH3:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 713FormamideHCID 6101p-Toluenesulfonic acidHCID 71462-PhenylpropanalHCID 8078Cyclohexane

Product 1

HCID 142952-Phenyl-1-propanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1st step). 1,340 parts of 2-phenylpropanal, 450 parts of formamide, 95 parts of p-toluenesulfonic acid and 420 parts by volume of cyclohexane are refluxed for 41/2 hours at 95°-98° C. in a stirred apparatus equipped with a reflux condenser and water separator; 144 parts of water are separated off. The reaction mixture is subjected to fractional distillation. The distillate is extracted with 500 parts by volume of ether. Distillation of the ether extract under reduced pressure gives 118 parts of unconverted 2-phenylpropanol, whilst crystallization of the extraction residue and the distillation residue gives 947 parts of N-(2-phenyl-prop-1-enyl)-formamide, corresponding to a yield of 64.5% of theory, based on 2-phenylpropanol converted.

Workup

  1. customequipped with a reflux condenser
  2. custom144 parts of water are separated off
  3. distillationThe reaction mixture is subjected to fractional distillation
  4. extractionThe distillate is extracted with 500 parts by volume of ether
  5. distillationDistillation of the ether
  6. extractionextract under reduced pressure

Sources & evidence

ORD record
ord-a4a4bca3803c4caaa8d1a7926d787360
Source dataset
uspto-grants-1982_02
Patent number
US04315869

Reaction notes

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