Benzene, 1-(phenylmethoxy)-4-(2-propen-1-yl)- synthesis
- Product Name:Benzene, 1-(phenylmethoxy)-4-(2-propen-1-yl)-
- CAS Number:90617-59-7
- Molecular formula:C16H16O
- Molecular Weight:224.3
Yield:90617-59-7 95%
Reaction Conditions:
with potassium carbonate in acetone; for 4 h;Reflux;
Steps:
1-Allyl-4-(benzyloxy)benzene (9a)
A mixture of 4-allylphenol 8a (3.0 g, 22.35 mmol, 1.50 equiv), K2CO3 (4.63 g, 33.52 mmol) and benzyl bromide (2.90 mL, 24.52 mmol, 1.10 equiv) in acetone (80 mL) was stirred under reflux for 4 h. The mixture was filtered to remove the solid and the filtrate was concentrated to dryness under reduced pressure. The resulting residue was dissolved in EtOAc (50 mL), and washed with water (50 mL) and brine (50 mL). The separated organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (0-5% EtOAc in hexanes) to obtain the title compound 9a as a colorless oil. Yield: (4.76 g, 95%); 1H NMR (400 MHz, CDCl3): δ 7.46-7.40 (m, 2H), 7.40-7.35 (m, 2H), 7.34-7.28 (m, 1H), 7.10 (d, 2H, J = 8.6 Hz), 6.91 (d, 2H, J = 8.6 Hz), 6.01-5.89 (m, 1H), 5.10-5.01 (m, 2H), 5.04 (s, 2H), 3.33 (d, 2H, J = 6.8 Hz); 13C NMR (100 MHz, CDCl3): δ 157.2, 137.8, 137.2, 132.4, 129.5, 128.5, 127.9, 127.4, 115.4, 114.8, 70.1, 39.3. The spectral data exactly matched with the literature data.1
References:
Devi, Runjun;Das, Sajal Kumar [Tetrahedron Letters,2018,vol. 59,# 23,p. 2281 - 2283] Location in patent:supporting information
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