m-Chloroperbenzoic acid → HCID 18546546, compound

To an ice-cold solution of 3-methylthio-1-propyl acrylate (18) (5.95 g, 37.1 mmol) in CH2Cl2 (80 mL), m-chloroperoxybenzoic acid (76.5 wt % 8.37 g, 37.1 mmol) was added in portions over a period of 1.5 hours. The progress of the reaction was monitored by TLC. Upon completion of the reaction, the solvent was evaporated under reduced pressure. The resulting sticky white solid was washed with water (2×100 mL) and filtered. The water washings were evaporated under reduced pressure to yield the crude product as a yellow oil. The crude product was purified by column chromatography (silica gel, ether, 20 wt % acetone/ether, 70 wt % acetone/ether) to afford colorless oil compound 23, namely methyl 3-(acryloyloxy)propyl sulfoxide (4.3 g, 66 wt %).

1. customUpon completion of the reaction
2. customthe solvent was evaporated under reduced pressure
3. washThe resulting sticky white solid was washed with water (2×100 mL)
4. filtrationfiltered
5. customThe water washings were evaporated under reduced pressure
6. customto yield the crude product as a yellow oil
7. customThe crude product was purified by column chromatography (silica gel, ether, 20 wt % acetone/ether, 70 wt % acetone/ether)

ORD record

ord-784b352666f74a8787b729b3b0fe1cff

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06552103B1