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

HRID 330367Notes

Reaction equation

HRID 330367 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]>C(O)C.[Pd]>[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)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.55 g of methyl 4-(4-hydrox-but-1-yn-1-yl)benzoate in 200 mL of ethanol is hydrogenated at 50 psi of hydrogen for 12 hours in the presence of 0.26 g (10% weight equivalent) of 5% palladium on charcoal. The reaction mixture is filtered through a silica gel pad, which is washed with ethanol, and concentrated to yield methyl 4-(4-hydroxybutyl)benzoate as an oil. IR (film) νmax 3390, 2965, 2920, 2850, 1705, 1605, 1568, 1520, 1500, 1410, 1387, 1362, 1308, 1286, 1250, 1160, 1055, 1013, 843, 755, and 695 cm-1 ; 1H NMR (CDCl3) delta 7.95 (d, J=8.1 Hz, 2H, Ar), 7.25 (d, J=8.1 Hz, 2H, Ar), 3.89 (s, 3H, --CH3), 3.65 (t, J=6.3 Hz, 2H, --CH2OH), 2.69 (t, J=7.5 Hz, 2H, benzyl), 1.66 (m, 4H, 2° aliphatic).

Workup

  1. filtrationThe reaction mixture is filtered through a silica gel pad, which
  2. washis washed with ethanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-adc8ae6b8345484a97e684b91d9c20dc
Source dataset
uspto-grants-1990_01
Patent number
US04895946

Reaction notes

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