ChemicalBook CAS DataBase List 4-(1-HYDROXY-ETHYL)-BENZOIC ACID

4-(1-HYDROXY-ETHYL)-BENZOIC ACID synthesis

11synthesis methods

Product Name:4-(1-HYDROXY-ETHYL)-BENZOIC ACID
CAS Number:97364-15-3
Molecular formula:C9H10O3
Molecular Weight:166.17

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Yield: 89%

Reaction Conditions:

with Iron(III) nitrate nonahydrate;2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;potassium chloride;oxygen in 1,2-dichloro-ethane at 25; for 48 h;Schlenk technique;

Steps:

General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 °C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)¹⁴ (69.9 mg, 57%) as a pale yellow solid.

References:

Jiang, Xingguo;Ma, Shengming [Synthesis,2018,vol. 50,# 8,p. 1629 - 1639]

586-89-0 Synthesis