4-(3-Hydroxyprop-1-ynyl)benzonitrile → 4-(3-Hydroxypropyl)benzonitrile

HRID 1071965Notes

Reaction equation

HRID 1071965 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.[H][H]>CCOC(C)=O.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]#[N:10])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 28227024-(3-Hydroxyprop-1-ynyl)benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 110841784-(3-Hydroxypropyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(3-hydroxyprop-1-ynyl)benzonitrile (2.0 g, 12.7 mmol) in EtOAc (25 mL), Pd/C (500 mg, 0.47 mmol) was added. A hydrogen balloon was placed over the reaction, and the reaction stirred for approximately four hours. An additional 200 mg (0.19 mmol) of Pd/C was added and the balloon was placed back over the reaction. Upon completion, the reaction mixture was filtered through a pad of celite and concentrated to give 4-(3-hydroxypropyl)benzonitrile which was used without further purifications.

Workup

  1. customthe balloon was placed back over the reaction
  2. filtrationUpon completion, the reaction mixture was filtered through a pad of celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3ef01e94514f47c3a7f9f00354d35008
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

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