4-Propylbenzoic acid → Methyl 4-propylbenzoate

Temperature

0 °C

To a 0° C. solution of 4-propylbenzoic acid (2 g, 12.18 mmol) in methanol (3.00 mL) and dichloromethane (10 mL) was added trimethylsilyldiazomethane (7.92 mL, 15.83 mmol), dropwise over a period of 5 min. Towards the end of the addition, the reaction mixture was pale yellow. The reaction was stirred at 0° C. for 30 min. and the excess diazo reagent was quenched by the slow addition of acetic acid at 0° C. (˜1.5 mL). The colorless solution was concentrated and partitioned between ether (20 mL) and sat. aq. sodium bicarbonate (10 mL). The ether layer was washed with brine (10 mL), dried over sodium sulfate and concentrated to yield methyl 4-propylbenzoate (2.1 g, 11.78 mmol, 97% yield) as a liquid. 1H NMR (400 MHz, CDCl3) δ ppm 7.95 (d, J=8.28 Hz, 2H) 7.24 (d, J=8.53 Hz, 2H) 3.90 (s, 3H) 2.61-2.67 (m, 2H) 1.59-1.71 (m, 1H) 0.94 (t, J=7.40 Hz, 1H).

1. additionTowards the end of the addition
2. customthe excess diazo reagent was quenched by the slow addition of acetic acid at 0° C. (˜1.5 mL)
3. concentrationThe colorless solution was concentrated
4. custompartitioned between ether (20 mL) and sat. aq. sodium bicarbonate (10 mL)
5. washThe ether layer was washed with brine (10 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated

ORD record

ord-3cdd155ac82741eca505d5f92c98c7c5

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216972B2