Dimethyl Sulfoxide → 3-(3,4-DIMETHOXY-PHENYL)-PROPIONALDEHYDE

Temperature

-45 °C

To a solution of oxalyl chloride(0.67 ml) in dichloromethane (80 ml) was added dropwise a solution of DMSO (1.18 ml) in dichloromethane(5 ml) at −78° C. To the mixture was added a solution of 1-(3,4-dimethoxyphenyl)propanol (1.50 g) in dichloromethane(25 ml) after 15 minutes. The mixture was stirred for an hour at −78° C. and for another hour at −45° C., then triethylamine(3.52 ml) was added. After stirring 20 minutes at 0° C., the mixture was quenched by a saturated aqueous NH4Cl solution, and extracted with dichloromethane. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of ethyl acetate and n-hexane (1:7 to 1:1) to give 3,4-dimethoxy-hydrocinnamaldehyde (1.05 g, 70.7%).

1. stirringAfter stirring 20 minutes at 0° C.
2. customthe mixture was quenched by a saturated aqueous NH4Cl solution
3. extractionextracted with dichloromethane
4. dry with materialThe organic layer was dried over MgSO4
5. customevaporated in vacuo
6. customThe residue was purified by a silica gel column chromatography
7. washeluting with a mixture of ethyl acetate and n-hexane (1:7 to 1:1)

ORD record

ord-995b7a257ef0496e8720d610e6ff65e4

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06812235B2