Acetone → 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one

To a solution of acetone (15.30 g, 263.76 mmol) in a mixture of ethanol (35 mL) and water (15 mL) were added sodium hydroxide (2.90 g, 72.54 mmol) and 4-hydroxy-3-methoxybenzaldehyde (5.01 g, 32.97 mmol). The reaction mixture was stirred at room temperature for 15 h. The reaction was cooled to 0° C. and quenched with 2.0 N hydrochloric acid until the solution became slightly acidic. The solution was extracted with ethyl acetate (4×100 mL). The combined organic layers were washed with water (50 mL) and saturated aqueous sodium chloride (50 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated at reduced pressure to afford 4-(4-hydroxy-3-methoxy-phenyl)but-3-ene-2-one (5.52 g, 87% yield) as a yellow solid: MS (EI) for C11H12O3: 193 (MH+).

1. temperatureThe reaction was cooled to 0° C.
2. customquenched with 2.0 N hydrochloric acid until the solution
3. extractionThe solution was extracted with ethyl acetate (4×100 mL)
4. washThe combined organic layers were washed with water (50 mL) and saturated aqueous sodium chloride (50 mL)
5. dry with materialThe organic layer was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated at reduced pressure

ORD record

ord-2782a4bd50764bc98b229d7c3e9ac000

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710038B2