Sodium borohydride → 3-(2-hydroxyethoxy)benzonitrile

HRID 606461Notes

Reaction equation

HRID 606461 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([O:9][CH2:10][C:11](OCC)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[BH4-].[Na+]>C(O)C>[OH:12][CH2:11][CH2:10][O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 24696095Ethyl (3-cyanophenoxy)acetate

Product 1

HCID 122221843-(2-hydroxyethoxy)benzonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl [(3-cyanophenyl)oxy]acetate obtained in Reference Example 29 (8.00 g, 39.0 mmol) and sodium borohydride (1.47 g, 39.0 mmol) in ethanol (120 mL) was stirred at 50° C. for 15 hr, and the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate and water, and the organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated to give the title compound as a white powder (5.85 g, 92%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate and water
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a21f18d2203143ca96e35a5397f7c9bf
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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