ChemicalBook CAS DataBase List Resveratrol

Resveratrol synthesis

8synthesis methods

Product Name:Resveratrol
CAS Number:501-36-0
Molecular formula:C14H12O3
Molecular Weight:228.24

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Yield:501-36-0 100%

Reaction Conditions:

Stage #1: (E)-1-(4-(benzyloxy)phenyl)-2-(3,5-bis(benzyloxy)phenyl)-ethenewith aluminum (III) chloride;triethylamine in chlorobenzene at 0 - 80; for 10 h;
Stage #2: with water in chlorobenzene at 0; for 2 h;Product distribution / selectivity;

Steps:

3

4 ml of chlorobenzene and 6 g of triethylamine (59.3 mmol) are introduced into a three- necked round-bottomed flask. A nitrogen atmosphere is applied, the mixture is cooled to 0-5⁰C and 4.9 g of anhydrous aluminium chloride (36.7 mmol) are introduced in small fractions at this temperature. The medium is brought to 50⁰C and is maintained at this temperature for 1 h, and then 2 g of (E)-3,5,4'-tribenzyloxystilbene (4 mmol) dissolved in 5 ml of chlorobenzene are added in 1 h at this temperature. This temperature is maintained for 4 h and then a temperature of 80°C is maintained for 4 h. The mixture is brought back to ambient temperature, separation by settling is carried out and the heavy phase is recovered and poured onto 20 ml of a 50/50 ice/water mixture. The medium is kept stirred for 2 h and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium bicarbonate solution and then with water and then concentrated to result in 0.93 g of crude (E)-resveratrol, i.e. a practically quantitative yield with respect to the starting tribenzylresveratrol.

References:

WO2009/43761,2009,A1 Location in patent:Page/Page column 10