PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]- synthesis
- Product Name:PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]-
- CAS Number:95041-90-0
- Molecular formula:C18H22O5
- Molecular Weight:318.36
![Phenol, 2-methoxy-5-[(1E)-2-(3,4,5-trimethoxyphenyl)ethenyl]-](/CAS/20200611/GIF/117048-62-1.gif)
117048-62-1
95041-90-0
General procedure for the synthesis of 2-methoxy-5-(3,4,5-trimethoxyphenethyl)phenol (SIT-1) from the compound (CAS:117048-62-1): compound CA-4 (1.0 g, 3.16 mmol) and 10% palladium-carbon catalyst (0.1 g) were dissolved in methanol (20 mL) and the reaction was stirred for 2 h at room temperature under hydrogen atmosphere. . Upon completion of the reaction, the palladium-carbon catalyst was removed by filtration and the filtrate was dried with anhydrous sodium sulfate and concentrated to afford the target product SIT-1 in 91% yield. The product was characterized by 1H NMR (500 MHz, CDCl3): δ 6.81 (d, 1H, J=3.0 Hz), 6.77 (d, 1H, J=8.0 Hz), 6.64-6.66 (m, 1H), 6.38 (s, 2H), 5.61 (s, 1H), 3.87 (s, 3H), 3.83 (s, 9H), 2.82 (s 4H).
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Yield:-
Steps:
Multi-step reaction with 5 steps
1: Lawesson's reagent
2: potassium hydroxide / ethanol / 12 h / 0 - 20 °C
3: m-chloroperoxybenzoic acid; NaHCO3 / CH2Cl2 / 12 h / 20 °C
4: 69 percent / water; potassium hydroxide; carbon tetrachloride / 2-methyl-propan-2-ol / 12 °C / Heating
5: 99 percent / H2 / Pd/C / ethyl acetate
References:
Robinson, James E.;Taylor, Richard J. K. [Chemical Communications,2007,# 16,p. 1617 - 1619]
![Phenol, 2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethynyl]-](/CAS/20210305/GIF/185698-55-9.gif)
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