3-(1-Naphthalenyl)-2-propenoic acid → 1-Naphthalenepropionic acid

HRID 567886

Reaction equation

HRID 567886 reaction equation
[C:1]1([CH:11]=[CH:12][C:13]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>[Pd].O1CCCC1>[C:1]1([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 983073-(1-Naphthalenyl)-2-propenoic acid

Product 1

HCID 952541-Naphthalenepropionic acidYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on carbon (1.00 g) was added to a suspension of 3-(1-naphthyl)acrylic acid (50.0 g) in tetrahydrofuran (500 ml). The mixture was hydrogenated at 6 atmospheres for 18 hours then filtered through a kieselguhr pad washing with ethyl acetate (3×100 ml). The filtrate was evaporated under reduced pressure to give the subtitle compound (50.0 g) as a solid.

Workup

  1. filtrationthen filtered through a kieselguhr pad
  2. washwashing with ethyl acetate (3×100 ml)
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cf66828f08a047888afe510c8cdcdcdd
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Linked notes

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