Veratraldehyde → 1'-Hydroxymethyleugenol

Temperature

0 °C

To a solution of 3,4-dimethoxybenzaldehyde (5.30 g, 31.9 mmol) in THF (50 mL) was added dropwise under a nitrogen atmosphere at 0° C. over a period of 30 min vinylmagnesium bromide (1 M in THF, 32 mL, 32 mmol) and stirred for 2 h at 0° C. followed by 1 h at ambient temperature. Further vinylmagnesium bromide (1 M in THF, 32 mL, 32 mmol) was added at 0° C. and the solution was stirred for 1 h at this temperature. The reaction mixture was added onto a mixture of ice (50 g) and aqueous ammonium chloride (saturated, 50 mL). The mixture was extracted with tert-butylmethylether and the organic layers were washed with water (50 mL) and brine (50 mL). Drying over sodium sulfate und purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (5.18 g, 84%) as a light yellow oil.

1. waitfollowed by 1 h at ambient temperature
2. stirringthe solution was stirred for 1 h at this temperature
3. extractionThe mixture was extracted with tert-butylmethylether
4. washthe organic layers were washed with water (50 mL) and brine (50 mL)
5. dry with materialDrying over sodium sulfate und purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

ORD record

ord-293dbb9a2737470f8fa0574453464b70

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829563B2