Acetic Acid → Methyl 4-(1-methoxy-1-oxopropan-2-yl)benzoate

Temperature

0 °C

A mixture of 35% potassium hydride in oil (6.04 g, equivalent to 2.11 g, 53 mmol of potassium hydride) in 240 mL of sieve dried tetrahydrofuran was cooled to 0° C. The cold mixture was treated with homoterephthalic acid dimethyl ester (10.0 g, 48 mmol). The mixture was stirred at 0° C. for 1 h. Methyl iodide (7.51 g, 53 mmol) was added and the mixture stirred at 0° C. for 30 min, then at room temperature for 16 h. The resulting mixture was treated with 4.8 mL of 50% acetic acid, then poured into 480 mL of water. The mixture was extracted with ether (2×250 mL). The ether extracts were combined, dried on magnesium sulfate, and concentrated to a brown oil, 15.67 g. Chromatography on 250 g of flash silica gel (10% ether in hexanes eluent) gave the product as a pale yellow oil, 7.24 g (67.9% theory). NMR (CDCl3): δ=7.56 (q, 4H, Ar); 2.78 (m, 7H, 2×CH3O+ArCH); 1.49 (d, 3H, CH3CH).

1. stirringthe mixture stirred at 0° C. for 30 min
2. waitat room temperature for 16 h
3. extractionThe mixture was extracted with ether (2×250 mL)
4. customdried on magnesium sulfate
5. concentrationconcentrated to a brown oil, 15.67 g

ORD record

ord-2b6d6c2d25d04f62bac57c8963bb4e88

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05374726