Ethyl Acetate → [2-(3-Hydroxypropyl)phenyl]acetonitrile

HRID 46990Notes

Reaction equation

HRID 46990 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[C:15]([CH2:17][C:18]1[CH:30]=[CH:29][CH:28]=[CH:27][C:19]=1[CH2:20][CH2:21][C:22](OCC)=[O:23])#[N:16].C(OCC)(=O)C>C1C=CC=CC=1>[OH:23][CH2:22][CH2:21][CH2:20][C:19]1[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=1[CH2:17][C:15]#[N:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 54486935Ethyl o-(cyanomethyl)hydrocinnamate

Product 1

HCID 22645929[2-(3-Hydroxypropyl)phenyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A 70% solution in benzene of sodium bis(2-methoxyethoxy)aluminum hydride (95.2 g., 0.33 mole of reagent) is added dropwise during one hour to a stirred solution of ethyl o-(cyanomethyl)hydrocinnamate (65.0 g., 0.3 mole) in benzene (250 ml.). The reaction mixture is held at 25°-28° C. by means of a cold water bath. The mixture is stirred at 25°-28° C. for 4 additional hours. Ethyl acetate (5 ml.) is added to destroy excess reducing agent. The mixture is then treated with 250 ml. ice-cold 5% hydrochloric acid. The benzene layer is separated, washed with water, and dried over sodium sulfate. Evaporation of the benzene in vacuo affords [2-(3-hydroxypropyl)phenyl]acetonitrile.

Workup

  1. customThe reaction mixture is held at 25°-28° C. by means of a cold water bath
  2. customto destroy excess
  3. additionThe mixture is then treated with 250 ml
  4. customThe benzene layer is separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the benzene in vacuo

Sources & evidence

ORD record
ord-97ce53f8627f46f5b5b2ca6a521c1693
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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