1-(BENZYLOXY)-3-ETHYNYLBENZENE synthesis

4synthesis methods

Product Name:1-(BENZYLOXY)-3-ETHYNYLBENZENE
CAS Number:128133-59-5
Molecular formula:C15H12O
Molecular Weight:208.26

10401-11-3
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Yield:128133-59-5 70%

Reaction Conditions:

Stage #1: 3-hydroxy phenylacetylenewith potassium carbonate in acetone; for 0.25 h;Reflux;
Stage #2: benzyl bromidewith potassium iodide in acetone; for 3 h;Reflux;

Steps:

Preparationof 1-(benzyloxy)-3-ethynylbenzene(19).

To a solution of 3-ethynylphenol(310.4 mg, 2.6 mmol) in acetone (10 mL) was added K₂CO₃(1.08 g, 7.8 mmol). The mixture was stirred at reflux for 15 min. KI (215.8 mg,1.3 mmol) and (bromomethyl)benzene (667.0 mg, 3.9mmol) were added to the above reaction mixture, and reaction mixture wasstirred at reflux for 3 h. The mixture was filtered and concentrated under reduced pressure. The residuewas purifiedby chromatography on silica gel, elution being carried out with ethyl acetateand hexanes. Compound 19 wasprepared in 70% yield as a colorless oil.¹H NMR (500 MHz, CDCl₃) δ 7.45 - 7.31 (m, 5H), 7.28 -7.18 (m, 1H), 7.13 - 7.08 (m, 2H), 6.98 (d, J = 7.2 Hz, 1H), 5.05 (s,2H), 3.06 (s, 1H). m/z (M+ 1)⁺ = 209.1.

References:

Chen, Zhen;Deng, Xiaoyun;Fujinaga, Masayuki;Hatori, Akiko;Hu, Kuan;Josephson, Lee;Kumata, Katsushi;Liang, Steven;Mori, Wakana;Murtas, Giulia;Pollegioni, Loredano;Rong, Jian;Shao, Tuo;Shao, Yihan;Van, Richard;Wey, Hsiao-Ying;Yu, Qingzhen;Zhang, Ming-Rong;Zhang, Yiding [Bioorganic and medicinal chemistry letters,2020,vol. 30,# 16] Location in patent:supporting information

10401-11-3
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$14.00/250mg

100-44-7 Synthesis