Veratryl alcohol → Veratryl chloride

Temperature

0 °C

3,4-dimethoxybenzyl alcohol (20 g, 119 mmol) was dissolved in toluene (60 ml) and cooled to 0° C. Thionyl chloride (7.48 g, 61.4 mmol) was added dropwise to the cooled solution of the alcohol over a period of 30 minutes, and the reaction was maintained at 0° C. for an additional 30 minutes. The reaction was quenched by pouring onto an ice/water mix (100 ml), and the organic phase was separated. The aqueous phase was then extracted into toluene (2×20 ml) and the combined toluene solution was dried over anhydrous sodium sulfate. The toluene was removed at reduced pressure to afford an oil which solidified upon standing, with a yield of 21 g. The material was characterized as a single spot by thin layer chromatography (TLC).

1. temperaturethe reaction was maintained at 0° C. for an additional 30 minutes
2. customThe reaction was quenched
3. additionby pouring onto an ice/water
4. additionmix (100 ml)
5. customthe organic phase was separated
6. extractionThe aqueous phase was then extracted into toluene (2×20 ml)
7. dry with materialthe combined toluene solution was dried over anhydrous sodium sulfate
8. customThe toluene was removed at reduced pressure
9. customto afford an oil which

ORD record

ord-182dff26fd8a47de90ddcafc14b88847

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895554B2