4-(4-Hydroxy-1-Butynyl)benzoic Acid Methyl Ester → Methyl 4-(4-hydroxybutyl)benzoate

HRID 2382544Notes

Reaction equation

HRID 2382544 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 146031084-(4-Hydroxy-1-Butynyl)benzoic Acid Methyl Ester

Product 1

HCID 14603109Methyl 4-(4-hydroxybutyl)benzoateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirring solution of 4-(4-hydroxy-but-1-ynyl)-benzoic acid methyl ester (6.29 g, 0.031 mol) in ethanol (60 mL) was added palladium on carbon (5 g, 10% on carbon) and the reaction mixture was hydrogenated at 50 psi. After 20 hours, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated to afford 4-(4-hydroxy-butyl)-benzoic acid methyl ester (5.67 g, 0.027 mol) as the desired product (89% yield). 1H (CDCl3, 600 MHz): δ 7.94 (2H, d, J=8.4 Hz), 7.24 (2H, d, J=8.4 Hz), 3.89 (s, 3H), 3.65 (2H, t, J=6.6 Hz), 2.65 (2H, t, J=7.8 Hz), 1.71 (2H, m), 1.58 (2H, m).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-17664bf7a5514bea91b3f8f714dfaf0b
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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