ChemicalBook CAS DataBase List 3-(1-NAPHTHYL)-PROPIONIC ACID

3-(1-NAPHTHYL)-PROPIONIC ACID synthesis

10synthesis methods

Product Name:3-(1-NAPHTHYL)-PROPIONIC ACID
CAS Number:3243-42-3
Molecular formula:C13H12O2
Molecular Weight:200.23

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Yield: 79%

Reaction Conditions:

Stage #1:diethyl (1-naphthylmethyl)malonate with ethanol;water;sodium hydroxideReflux;
Stage #2: with hydrogenchloride in water; pH=Ca. 1

Steps:

3-(1-Naphthyl)propanoic acid (10).
To an aqueous solution of NaOH (3 mL, 15 N) was added ethanol (12 mL, 95%) and compound 9 (1.00 g, 3.33 mmol). The mixture was heated to reflux overnight. Then the reaction was concentrated in vacuo. The residual was dissolved in water (15 mL) and washed with ether (3×20 mL). The aqueous phase was treated with concentrated HCl to adjust the pH to about 1 and extracted with ether (3×20 mL). The combined organic phase was dried over Na₂SO₄ and concentrated in vacuo. The resulting solid was recrystallized from CHCl₃ to give 10 (0.53g, 79%) as a white solid.¹H NMR (400 MHz, CDCl₃) δ 8.03 (d, J = 8.3, 1H), 7.87 (d, J = 7.9, 1H), 7.75 (d, J = 7.9, 1H), 7.52 (m, 2H), 7.44 - 7.30 (m, 2H), 3.52 - 3.39 (m, 2H), 2.90 - 2.78 (m, 2H);¹³C NMR (101 MHz, CDCl₃) δ 178.20, 136.08, 133.89, 131.53, 128.94, 127.28, 126.18, 125.92, 125.67, 125.58, 123.27, 34.70, 27.80.

References:

Yan, Hao;Li, Zhi-Fen;Guo, Zhi-Fo;Lu, Zhong-Lin;Wang, Feng;Wu, Li-Zhu [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 2,p. 801 - 808] Location in patent:supporting information; experimental part