Potassium Hydroxide → 3-(3-Ethynylphenyl)propan-1-ol

HRID 1021091Notes

Reaction equation

HRID 1021091 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]#[C:12]C(C)(O)C)[CH:8]=[CH:9][CH:10]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[C:11]([C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH:10]=[CH:9][CH:8]=1)#[CH:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 576085154-(3-(3-Hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol

Product 1

HCID 576083943-(3-Ethynylphenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(3-(3-hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol (49) (0.750 g, 3.4 mmol) in toluene (50 mL) was added powdered KOH (0.390 g, 7 mmol). The resulting mixture was heated at reflux for 45 min. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure to 10-15 mL volume and partitioned between EtOAc and water. The combined organics were washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (15% EtOAc-hexanes) gave 3-(3-ethynylphenyl)propan-1-ol (50) as a light brown oil. Yield (0.272 g, 49%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 45 min
  3. concentrationthe reaction mixture was concentrated under reduced pressure to 10-15 mL volume
  4. custompartitioned between EtOAc and water
  5. washThe combined organics were washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography (15% EtOAc-hexanes)

Sources & evidence

ORD record
ord-e18dd82fd30e4ce99054621421e18246
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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