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

HRID 1618384Notes

Reaction equation

HRID 1618384 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 (10) (0.750 g, 3.4 mmol) in toluene (50 mL) was added powdered KOH (0.390 g, 7 mmol). The resulting mixture was heated to reflux for 45 min, concentrated under reduced pressure to 10-15 mL and diluted with EtOAc (100 mL). The solution was washed with water (2×100 mL) and brine (50 mL), dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography gave 3-(3-ethynylphenyl)propan-1-ol (11) as a light brown oil. Yield (0.272 g, 49%): 1H NMR (400 MHz, DMSO-d6) δ 7.24-7.32 (m, 4H), 4.49 (t, J=5.2 Hz, 1H), 4.15 (s, 1H), 3.39 (dt, J=6.4, 5.6 Hz, 2H), 2.60 (t, J=7.6 Hz, 2H), 1.66-1.73 (m, 2H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 45 min
  3. concentrationconcentrated under reduced pressure to 10-15 mL
  4. additiondiluted with EtOAc (100 mL)
  5. washThe solution was washed with water (2×100 mL) and brine (50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-7f548c55cba444f08d4e7dc4f23a4585
Source dataset
uspto-grants-2014_07
Patent number
US08766007B2

Reaction notes

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