ChemicalBook CAS DataBase List Glycitein

Glycitein synthesis

10synthesis methods

Product Name:Glycitein
CAS Number:40957-83-3
Molecular formula:C16H12O5
Molecular Weight:284.26

124-63-0

Ethanone, 1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-

79744-58-4

40957-83-3

Under nitrogen protection, boron trifluoride ethyl ether complex (1.6 mL, 13.13 mmol) was slowly added to an anhydrous N,N-dimethylformamide (10 mL) solution of deoxybenzene coupling (0.6 g, 2.19 mmol). After 15 min of reaction, anhydrous N,N-dimethylformamide (2 mL) solution of methanesulfonyl chloride (0.84 mL, 10.95 mmol) was added dropwise. The reaction mixture was heated and stirred in an oil bath at 70°C for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice-cooled saturated aqueous sodium acetate solution (50 mL). The precipitated solid was collected by filtration and recrystallized from 70% ethanol to afford 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-benzopyran-4-one as a yellow solid (0.53 g, 85% yield) with a melting point of 336-338°C. The product structure was determined by 1H NMR. The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6) and mass spectrometry (EI, 70 eV): 1H NMR δ 10.63 (br s, 1H, 7-OH), 9.54 (br s, 1H, 4'-OH), 8.27 (s, 1H, H-2), 7.41 (s, 1H, H-5), 7.37 (d, J = 8.7 Hz. 2H, H-2', 6'), 6.92 (s, 1H, H-8), 6.79 (d, J = 8.7 Hz, 2H, H-3', 5'), 3.86 (s, 3H, OCH3); mass spectra m/z 284 (M+, 24%), 283 (100), 268 (15), 255 (20), 212 (41), 171 (15).

621-59-0 Synthesis

621-59-0
658 suppliers
$9.00/1g

40957-83-3
282 suppliers
$35.00/5mg

Yield:-

Steps:

Multi-step reaction with 4 steps
1.1: H₂O₂; SeO₂ / CH₂Cl₂ / 16 h / 20 °C
2.1: 4.7818 g / aq. K₂CO₃ / methanol / 1 h / 20 °C
3.1: 77 percent / BF₃*Et₂O / 0.17 h / Heating
4.1: 0.01 h / microwave irradiation
4.2: 26 percent / methanesulfonyl chloride / 0.02 h / microwave irradiation