ChemicalBook CAS DataBase List 4-decylphenol

4-decylphenol synthesis

11synthesis methods

Product Name:4-decylphenol
CAS Number:2985-57-1
Molecular formula:C16H26O
Molecular Weight:234.38

14353-77-6
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2985-57-1
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Yield:2985-57-1 82%

Reaction Conditions:

Stage #1: 1-(4-hydroxy-phenyl)-decan-1-onewith hydrazine hydrate in diethylene glycol dimethyl ether at 250; for 2 h;
Stage #2: with potassium hydroxide in diethylene glycol dimethyl ether at 190; for 4 h;

Steps:

4-Decylphenyl 2,3-dihydroxybenzoate ( B7 )

Phenol (1.83 g, 19.5 mmol) was added to decanoyl chloride (4.08 g, 21.4 mmol) , stirred at 80 until bubbles were stopped, aluminum trichloride (2.85 g, 21.4 mmol) was added, reflux was performed at 130 for 1 h. When cooled to room temperature, 1 M HCl solution was added to the mixture slowly to quench the reaction, then ethyl acetate was added for dilution, the organic phase was washed with 1 M HCl, saturated NaHCO₃ and saturated NaCl successively, and dried with anhydrous Na₂SO_4.Rotary evaporation was conducted to remove solvent to obtain intermediate (7) as white solid .The product is not purified and characterized, and is directly used for the next step. The intermediate (7) (0.24 g, 0.96 mmol) and hydrazine hydrate (1 ml) were added to diethylene glycol (6 mL), which was stirred at 250 for 2 h and cooled to room temperature. Potassium hydroxide (0.27 g, 4.80 mmol) was added and stirred at 190 for 4 h to remove the excess hydrazine hydrate. When cooled to room temperature, water (27 mL) was added for dilution, and washed twice with ethyl acetate. The water layer was adjusted to acidic with concentrated hydrochloric acid, and extracted three times with ethyl acetate. The combined organic phase was dried with anhydrous Na₂SO₄ , then filtered and concentrated in vacuo, the crude material was purified by flash chromatography to afford the intermediate (8) as white solid (185 mg, 82%). ¹H NMR (400 MHz, DMSO-d6): δ 9.15 (s, 1H), 6.98 (d, J = 8.0 Hz, 2H), 6.68 (d, J = 8.0 Hz, 2H), 2.47 (t, J = 7.4 Hz, 2H), 1.57-1.47 (m, 2H), 1.34-1.22 (m, 14H), 0.88 (t, J = 6.8 Hz, 3H).

References:

Wang, Zhenkang;Ma, Chunhua;Wang, Yujie;Xiao, Qiang;Xu, Chenghui;Li, Yingxia [Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,# 22,art. no. 126685] Location in patent:supporting information

112-13-0 Synthesis