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

HRID 2172748Notes

Reaction equation

HRID 2172748 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-f58a7bcae92b482c96c2cc9af7e0e315
Source dataset
uspto-grants-2015_06
Patent number
US09056849B2

Reaction notes

Loading…