Acetovanillone → HCID 54457755, compound

To a solution of acetovanillone (8.31 g, 50 mmol) and 2.81 g KOH (50 mmol) in H2O (34 mL), at 0°, is added a solution of dimethylthiocarbamoyl chloride (8.28 g, 67 mmol) in THF (14 mL), dropwise, at such a rate as to keep the reaction temperature below 12°. The reaction mixture is warmed to room temperature, and stirred for 30 minutes. It is then diluted with 1 N NaOH (100 mL) and extracted with EtOAc (3×80 mL). The combined organic phase is washed with H2O (1×100 mL) and brine (1×50 mL), dried over MgSO4, and concentrated in vacuo to give dimethylthiocarbamic acid O-(4-acetyl-2-methoxy-phenyl) ester. To a thick walled pyrex tube is aded dimethylthiocarbamic acid O-(4-acetyl-2-methoxy-phenyl) ester (9.81 g, 38.77 mmol). The tube is flushed with nitrogen, sealed, and then heated to 250° for 1 hour. After cooling, the residue is chromatographed (silica gel, 1:1 EtOAc/hexane) to yield dimethylthiocarbamic acid S-(4-acetyl-2-methoxy-phenyl) ester.

1. customthe reaction temperature below 12°
2. extractionextracted with EtOAc (3×80 mL)
3. washThe combined organic phase is washed with H2O (1×100 mL) and brine (1×50 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo

ORD record

ord-82f2781546fe47abbc00106a115486e5

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06291530B1