Diethyl Ether → 1-(5-Chloro-2,3-dimethoxyphenyl)ethanol

Temperature

33 °C

To a mixture of 5-chloro-2,3-dimethoxybenzaldehyde (339, 1.69 mol) in TBME (5.6 L) was added 3M methylmagnesium bromide in ether (660 mL, 1.98 mol) over 1 hour at 9 to 12° C. The mixture was warmed at 33° C. for 1 hour 20 minutes. There was significant starting material present so more methylmagnesium bromide was added (590 mL, 1.77 mol) over 1 hour 20 minutes with the reaction temperature at 33° C. The reaction was cooled to room temperature overnight and poured into ammonium chloride (20 wt %, 3 kg) over 5 minutes. The temperature rose from 11 to 28° C. The reaction flask was rinsed with ammonium chloride solution (500 mL) and TBME (250 mL). The layers were separated and the organic layer was concentrated to an orange yellow thick oil. Yield: 348 g (96% yield, 94% purity).

1. additionwas added (590 mL, 1.77 mol) over 1 hour 20 minutes with the reaction temperature at 33° C
2. temperatureThe reaction was cooled to room temperature overnight
3. customrose from 11 to 28° C
4. washThe reaction flask was rinsed with ammonium chloride solution (500 mL) and TBME (250 mL)
5. customThe layers were separated
6. concentrationthe organic layer was concentrated to an orange yellow thick oil

ORD record

ord-f6e6fe890c894580bd2710ff3326b314

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604021B2