Hydrochloric Acid → 3-(3,4-Dimethoxyphenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one

Temperature

0 °C

A solution of 3,4-Dimethoxybenzaldehyde (16.6 g, 100 mmol) in EtOH (75 mL) was treated with 3-Hydroxyacetaphenone (13.6 g, 100 mmol) and the resulting solution cooled to 0° C. in an ice bath. A 200 mL solution of aqueous KOH (28 g, 500 mmol) was added slowly and the resulting bright red solution was allowed to stir overnight (16 h) at room temperature. The mixture was then acidified to pH 5 by the dropwise addition of concentrated HCl and the resulting suspension extracted with EtOAc (2×200 mL). The combined organic extract was washed with a saturated NaCl solution (2×100 mL), dried over MgSO4, filtered, evaporated, and flash chromatographed (silica gel, 30% 50% EtOAc/hexanes) to give crude material. The crude solid was crystallized from EtOAc to afford 13.9 g (49%) of a yellow colored solids: IR (neat) 3420, 1650, 1575, 1510, 1265, 1140 cm-1 ; 1H NMR (CDCl3, 300 MHz) 7.80 (d, J=15.6 Hz, 1H), 7.68 (s, 1H), 7.59, (d, J=7.7 Hz, 1H), 7.42-7.36 (m, 2H), 7.24 (dd, J=8.3, 1.8 Hz, 1H), 7.16-7.13 (m, 2H), 6.90 (d, J=8.3 Hz, IH), 6.82 (s, 1H), 3.95 (s, 3H), 3.94 (s, 3H); 13C NMR (CDCl3, 75 MHz) 191.3. 157.0, 152.0, 149.7, 146.1, 140.1, 130.2, 128.2, 123.8, 121.2, 120.7, 120.3, 115.7, 111.6, 110.7, 56.4.

1. extractionthe resulting suspension extracted with EtOAc (2×200 mL)
2. extractionThe combined organic extract
3. washwas washed with a saturated NaCl solution (2×100 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customflash chromatographed (silica gel, 30% 50% EtOAc/hexanes)
8. customto give crude material
9. customThe crude solid was crystallized from EtOAc

ORD record

ord-3ad74cd41ebf4d0b8af5b999ccaa9e7e

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06150527