Methyl 4-(3-hydroxyprop-1-ynyl)benzoate → Methyl 4-(3-hydroxypropyl)benzoate

HRID 458995

Reaction equation

HRID 458995 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH2:12][OH:13])=[CH:6][CH:5]=1>CCOC(C)=O.CO.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 4448596Methyl 4-(3-hydroxyprop-1-ynyl)benzoate

Product 1

HCID 14425137Methyl 4-(3-hydroxypropyl)benzoateYield 92.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3-hydroxy-prop-1-ynyl)-benzoic acid methyl ester (12.65 g) in EtOAc (75 mL) and MeOH (75 mL) was hydrogenated at 50 psi on a Parr shaker in the presence of 10% palladium on carbon (2 g) for 24 h. The catalyst was removed by filtration through Celite® and the filtrate was concentrated. The reaction was repeated by adding 10% palladium on carbon (2 g) and hydrogenating on a Parr shaker for 24 h. After filtering through Celite®, the solution was concentrated in vacuo to provide 4-(3-hydroxy-propyl)-benzoic acid methyl ester (11.98 g).

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated
  3. additionby adding 10% palladium on carbon (2 g)
  4. filtrationAfter filtering through Celite®
  5. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-bac5b1d992734f90a9cc3a977a98c391
Source dataset
uspto-grants-2007_03
Patent number
US07192979B2

Linked notes

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