Benzyl Alcohol → 3-(Benzyloxy)-2-methylpropanenitrile

HRID 972057Notes

Reaction equation

HRID 972057 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:11](#[N:15])[C:12]([CH3:14])=[CH2:13].OS(O)(=O)=O>CCOCC>[CH2:1]([O:8][CH2:13][CH:12]([CH3:14])[C:11]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 24758Sodium hydrideHCID 31368Methacrylonitrile

Product 1

HCID 135315353-(Benzyloxy)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Benzyl alcohol (108 g.; 1 mole) was stirred and treated with 0.3 g. of 50% by weight sodium hydride in a mineral oil dispersion. To the resulting solution was added dropwise 415 ml. (335 g.; 5 moles) of methacrylonitrile over a 40 minute period, at room temperature. The reaction mixture was heated at 60°-65° C. for 5 hours then cooled, acidified with 1 N aqueous H2SO4 and diluted with ether. The ether solution was washed twice with saturated brine then dried, filtered and concentrated in vacuo. Distillation of the residue gave, after removal of low boiling materials, 149.3 g. (85%) of rac. 3-benzyloxy-2-methylpropionitrile as a colorless liquid, b.p. 90°-93° C. (0.02 mm Hg.).

Workup

  1. additiontreated with 0.3 g
  2. additionTo the resulting solution was added dropwise 415 ml
  3. customat room temperature
  4. temperatureThe reaction mixture was heated at 60°-65° C. for 5 hours
  5. temperaturethen cooled
  6. washThe ether solution was washed twice with saturated brine
  7. customthen dried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. distillationDistillation of the residue
  11. customgave
  12. customafter removal of low boiling materials, 149.3 g

Sources & evidence

ORD record
ord-ce25bfa1f8e94ccab37d6328e929a6c2
Source dataset
uspto-grants-1979_07
Patent number
US04163021

Reaction notes

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