4-Hydroxybenzaldehyde → HCID 87106121, compound

Temperature

80 °C

To a 100 mL RB flask fitted with magnetic stirrer was charged 20 mL of acetonitrile. To the stirred solvent was added 4-hydroxy-benzaldehyde (0.21 g, 1.72 mmol) and K2CO3 (0.46 g, 3.33 mmol). Then it was stirred for 5 min. 2-Bromo-1-phenyl-ethanone o-methyl-oxime (0.4 g, 1.7 mmol) was added. Then RM was heated to 80° C. and stirred at this temperature for 5 h. After completion of the reaction (reaction monitored by TLC), RM was concentrated by removal of the acetonitrile, water (10 mL) was added, and the mixture was extracted with ethyl acetate (20 mL×2). The organic layer washed with saturated brine solution (20 mL) and dried over anhydrous Na2SO4 and evaporated to dryness to get the title compound (0.4 g, Yield: 87.5%): MS (ESI, 120 eV): m/z=270.1 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 9.80 (s, 1H), 7.72-7.75 (d, 2H), 7.655-7.59 (m, 2H), 7.27-7.29 (m, 3H), 6.92-6.95 (d, 2H), 5.22 (s, 2H), 4.01 (s, 3H).

1. customTo a 100 mL RB flask fitted with magnetic stirrer
2. stirringstirred at this temperature for 5 h
3. customAfter completion of the reaction (reaction monitored by TLC), RM
4. concentrationwas concentrated by removal of the acetonitrile, water (10 mL)
5. additionwas added
6. extractionthe mixture was extracted with ethyl acetate (20 mL×2)
7. washThe organic layer washed with saturated brine solution (20 mL)
8. dry with materialdried over anhydrous Na2SO4
9. customevaporated to dryness

ORD record

ord-f1f8ae1fd1c74d4e9506c0708683c1e7

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2