3-(6,7-Dimethyl-2-naphthoyl)propanoic acid → 4-(6,7-Dimethyl-2-naphthyl)butanoic acid

HRID 375010Notes

Reaction equation

HRID 375010 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]=[C:7]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=O)[CH:6]=[CH:5]2>[Pd].C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]=[C:7]([CH2:13][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 229045903-(6,7-Dimethyl-2-naphthoyl)propanoic acid

Product 1

HCID 229045924-(6,7-Dimethyl-2-naphthyl)butanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

The β-isomer, 3-(6,7-dimethyl-2-naphthoyl)propanoic acid (6.58 g, 0.026 mole) was dissolved into 200 ml of THF in a hydrogenation pressure bottle. To the solution was carefully added 30% Pd/C (700 mg). The whole mixture was shaken for 15 hrs under H2 (40 psi) at room temperature. After releasing pressure, Pd/C was removed by passing the THF solution through the celite pad. The solution was concentrated to afford 4-(6,7-Dimethyl-2-naphthyl)butanoic acid as a gray solid material (6.21 g, 0.026 mole, 100% yield). mp 141.0°-142.0° C., 1H NMR (CDCl3)δ 1.98-2.12 (m,2H), 2.36-2.41 (m,8H), 2.81 (t, J=7.4 Hz,2H), 7.22 (d, J=8.3 Hz,1H), 7.49-7.55 (m,3H), 7.65 (d, J=8.3 Hz,1H), IR (KBr) cm-1 3700-3450, 2920, 1698, Anal. Calcd. for C 16 H18O2 : C, 79.31; H, 7.49. Found: C, 79.28; H, 7.49.

Workup

  1. customwas removed
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-0e03e8b091da47c193b79db2067d41f4
Source dataset
uspto-grants-1996_01
Patent number
US05484530

Reaction notes

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