methyl 4-(4-hydroxy-1-butynyl)phenylacetate → methyl 4-(4-hydroxybutyl)phenylacetate

HRID 2289117Notes

Reaction equation

HRID 2289117 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[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:7]=[CH:8][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 10536788methyl 4-(4-hydroxy-1-butynyl)phenylacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 10262968methyl 4-(4-hydroxybutyl)phenylacetateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl 4-(4-hydroxybutyn-1-yl)phenylacetate (178 mg, 0.82 mmole) and 10% palladium on carbon (30 mg) in ethanol (2 mL) were stirred under a balloon of hydrogen for 3 days at room temperature. The mixture was filtered and the filtrate concentrated in vacuo to give the title compound (181 mg) as an oil. NMR (CDCl3): δ 1.52 (s, 1H); 1.64 (m, 2H); 1.71 (m, 2H); 2.65 (t, 2H); 3.61 (s, 2H); 3.68 (t, 2H); 3.71 (s, 3H); 7.15 (d, 2H); 7.21 (d, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-91200ccefc1c4202b632844557a50b26
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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