ChemicalBook CAS DataBase List (E)-2-methoxy-4-(prop-1-enyl)phenol

(E)-2-methoxy-4-(prop-1-enyl)phenol synthesis

11synthesis methods

Product Name:(E)-2-methoxy-4-(prop-1-enyl)phenol
CAS Number:5932-68-3
Molecular formula:C10H12O2
Molecular Weight:164.2

97-53-0 Synthesis

97-53-0
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$5.00/25g

5932-68-3
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$59.10/1ml

Yield:5932-68-3 95.9%

Reaction Conditions:

with Grotjahn’s catalyst at 20; for 0.333333 h;Catalytic behavior;Glovebox;Inert atmosphere;Green chemistry;diastereoselective reaction;Reagent/catalyst;

Steps:

Eugenol to (E)-Isoeugenol
In a glove box, a 50 mL round bottomed flask equipped with a magnetic stir bar was added eugenol (16.43 g, 0.1 mol), capped with a rubber septum, and removed from the glove box. In an inert atmosphere glove box, catalyst 1(60.5 mg, 0.101 mmol, 0.1 mol%) was measured into a scintillation vial, capped, and brought out of the glove box. The septum was removed from the reaction flask and thecatalyst was quickly added, followed by bubbling nitrogen through the liquid to remove any air that had entered. Aliquots (ca. 5 μL) were removed from the reaction at 5, 10,and 20 minutes using a gastight syringe and analyzed by 1H NMR for completion. Full conversion of eugenol to (E)-isoeugenol occurred after 20 minutes, and the product was isolated by vacuum distillation (2 torr, 98 oC) to afford 15.76 g (95.9%) of (E)-isoeugenolas a clear, colorless oil. To accurately determine amount of starting material remaining,105.1 mg of the distillate was weighed out in an NMR tube containing 0.5-0.7 mL CDCl3and analyzed by 1H NMR; percentages were calculated assuming a two-component mixture (eugenol/isoeugenol), using residual chloroform peak as internal standard. Peaks used: eugenol 5.11 ppm (2H), 3.34 ppm (2H); isoeugenol 6.36 ppm (1H), 6.12 ppm (1H), 1.90 ppm (3H).

References:

Larsen, Casey R.;Paulson, Erik R.;Erdogan, Gulin;Grotjahn, Douglas B. [Synlett,2015,vol. 26,# 17,art. no. ST-2015-B0231-L,p. 2462 - 2466] Location in patent:supporting information

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