Dimethylformamide → 3-(3-Methoxyphenyl)-3-methylbutanoic acid

Temperature

100 °C

The 5-(2-(3-methoxyphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione 85.C (0.313 g, 1.1 mmol) was dissolved in DMF (1.50 mL, 19 mmol). To the solution was added water (0.15 mL, 8.3 mmol). The resulting solution was then heated to 100° C. and stirred for four hours. The reaction was cooled to room temperature and then diluted with water. The mixture was extracted with EtOAc (2×50 mL). The combined organic layers were then washed with 1N lithium chloride solution (1×20 mL) and brine (1×20 mL) and dried over magnesium sulfate. The filtrate was then concentrated to give crude 3-(3-methoxyphenyl)-3-methylbutanoic acid 85.D (0.247 g, 111% yield) that was used directly in the following reaction. MS ESI (pos.) m/e: 226.1 (M+H2O)+.

1. temperatureThe reaction was cooled to room temperature
2. extractionThe mixture was extracted with EtOAc (2×50 mL)
3. washThe combined organic layers were then washed with 1N lithium chloride solution (1×20 mL) and brine (1×20 mL)
4. dry with materialdried over magnesium sulfate
5. concentrationThe filtrate was then concentrated

ORD record

ord-d87253ef0b0249d2b0a373d301e70704

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030354B2