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

HRID 1296458Notes

Reaction equation

HRID 1296458 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) δ 1.59 (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-1ba50fcee08243769a420de2689ca589
Source dataset
uspto-grants-2007_07
Patent number
US07247636B2

Reaction notes

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