4-(2,4-Dimethoxyphenyl)-but-3-yn-1-ol → 4-(2,4-Dimethoxyphenyl)butan-1-OL

HRID 25108Notes

Reaction equation

HRID 25108 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]#[C:12][CH2:13][CH2:14][OH:15]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][CH2:14][OH:15]

Participants

4

Reactant 1

HCID 225661274-(2,4-Dimethoxyphenyl)-but-3-yn-1-ol

Product 1

HCID 225661304-(2,4-Dimethoxyphenyl)butan-1-OLYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 75 (4.2 g, 0.022 mol) in ethanol (approx. 200 mL) was added palladium (5% wet on activated carbon, 1 g). Then the mixture was hydrogenated at 40 psi overnight at room temperature. The mixture was filtered through a pad of silica gel and the solvent was evaporated to give 76 (4.15 g, 97%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ1.59 (m, 4H), 2.55 (m, 2H), 3.79 (s, 6H), 6.43 (m, 2H), 7.00 (m, 1H).

Workup

  1. customwas hydrogenated at 40 psi overnight at room temperature
  2. filtrationThe mixture was filtered through a pad of silica gel
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5d4943a1e0074bd496e2312f2a425553
Source dataset
uspto-grants-2005_02
Patent number
US06858614B2

Reaction notes

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