Dimethyl Sulfoxide → 6-Methyl-3-hexoxymethylcyclohexene

A 500 mL round bottom flask equipped with a mechanical stirrer was charged with 18.9g (0.15 mol) 6-methyl-3-cyclohexenemethanol, and 130 mL of DMSO. Sodium hydride (4.22 g, 95% in purity; 0.167 mol) was slowly added to above mixture in ice bath over 25 min. After the above mixture was reacted at room temperature for 2 hrs. Hexyl bromide (27.3 g, 0.165 mol) was slowly added to the above mixture over 25 min. The reaction was carried at room temperature for 1 hr, then 70° C overnight. The reaction mixture was added to water (150 mL), and then extracted with chloroform (3×150 mL), washed with water (2×150 mL), 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 2 hrs
3. custom70° C overnight
4. extractionextracted with chloroform (3×150 mL)
5. washwashed with water (2×150 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-b1efc1c3bb5b424ba5850d9b2a0e068e

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07018559B2