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

HRID 1108442Notes

Reaction equation

HRID 1108442 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.[H][H]>[Pd].C(O)C>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 146031084-(4-Hydroxy-1-Butynyl)benzoic Acid Methyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 14603109Methyl 4-(4-hydroxybutyl)benzoateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr flask was charged with 3.25 g (15.98 mmol) of methyl 4-(4-hydroxy-1-butynyl)benzoate (Taylor et al. J. Org. Chem., 1990, 55, 3222-3227) and 0.26 g (8% wt equivalent) of 10% palladium-on-carbon catalyst in 40 mL of ethanol. Hydrogenation was carried out at 50 psi of hydrogen for 18 hours. The mixture was filtered through a silica gel pad that was subsequently washed with ethanol. The combined filtrates were concentrated under reduced pressure to give 3.20 g (97%) of methyl 4-(4-hydroxybutyl)benzoate as a light yellow oil. 1H NMR (CDCl3) δ 1.51 (1H, s), 1.57-1.82 (4H, m), 2.74 (2H, t, J=7.3 Hz), 3.71 (2H, t, J=6.0 Hz), 3.94 (3H, s), 7.27 (2H, d, J=8.0 Hz), 7.99 (2H, d, J=8.0 Hz).

Workup

  1. filtrationThe mixture was filtered through a silica gel pad that
  2. washwas subsequently washed with ethanol
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-e4006aa2e16442819bcca3f2ed0050d1
Source dataset
uspto-grants-2000_05
Patent number
US06066732

Reaction notes

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