ETHYL 4-(4-METHOXY-3-METHYLPHENYL)-4-OXOBUTANOATE synthesis
- Product Name:ETHYL 4-(4-METHOXY-3-METHYLPHENYL)-4-OXOBUTANOATE
- CAS Number:2954-68-9
- Molecular formula:C14H18O4
- Molecular Weight:250.29
33446-14-9
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Yield:2954-68-9 20.6 g (84%)
Reaction Conditions:
with sodium hydroxide;sulfuric acid in ethanol;water;
Steps:
4-(4-Methoxy-3-methylphenyl)-4-oxo-butyric acid ethyl ester (Compound 3)
4-(4-Methoxy-3-methylphenyl)-4-oxo-butyric acid ethyl ester (Compound 3) To a solution of 4-(4-methoxy-3-methylphenyl)-4-oxobutyric acid (Compound 2, 21.75 g, 98.0 mmol) in absolute ethanol (200 mL) was added 10 drops of concentrated H2SO4. The resulting solution was refluxed for 3 days, then cooled to room temperature, treated with 30 mL of NaOH 2N, diluted with 50 mL of water, and extracted 3 times with EtOAc. The combined organic layers were washed with brine, and dried over MgSO4, and filtered. The solvent was removed to afford 20.6 g (84%) of the title compound as a yellow solid. PNMR (300 MHz, CDCl3) δ1.24 (t, 3 H, J=6.7 Hz), 2.24 (s, 3 H), 2.73 (t, 2 H, J=6.67 Hz), 3.26 (t, 2 H, J=6.7 Hz), 3.90 (s, 3 H), 4.14 (t, 2 H, J=7.0 Hz), 6.84 (d, 1 H, J=8.6 Hz), 7.79 (s, 1 H), 7.85 (d, 1 H, J=8.5 Hz).
References:
US2003/166932,2003,A1
