Dimethyl Sulfoxide → 3-Decyloxymethylcyclohexene

A 500 mL round bottom flask equipped with a mechanical stirrer was charged with 23.7g (0.15 mol) decyl alcohol, and 150 mL of DMSO. Sodium hydride (4.22 g, 95% in purity; 0.167 mol) was slowly added to above mixture in an ice bath over 20 min. After the above mixture was reacted at room temperature for 3 hrs, the reaction mixture was cooled to room temperature. 3-Cyclohexene-1-methanol tosylate (39.9 g, 0.15 mol) was slowly added to the above mixture over 20 min. The reaction was carried at room temperature overnight, then 80° C. for 3 hrs. The reaction mixture was added to water (150 mL), and then extracted with chloroform (3×150 niL), washed to water (2×100 mL) and dried with sodium sulfate. The solvent was evaporated and the residue distilled to give pure product.

1. customA 500 mL round bottom flask equipped with a mechanical stirrer
2. customAfter the above mixture was reacted at room temperature for 3 hrs
3. wait80° C. for 3 hrs
4. extractionextracted with chloroform (3×150 niL)
5. washwashed to water (2×100 mL)
6. dry with materialdried with sodium sulfate
7. customThe solvent was evaporated
8. distillationthe residue distilled
9. customto give pure product

ORD record

ord-38c01c9fe730490bb9f82ef733d010fe

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07018559B2