Dimethyl Sulfoxide → HCID 22222982, compound

HRID 1744712Notes

Reaction equation

HRID 1744712 reaction equation
[C:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CS(C)=O.[H-].[Na+].S(C1C=CC(C)=CC=1)(O[CH2:19][CH:20]([CH2:25][CH3:26])[CH2:21][CH2:22][CH2:23][CH3:24])(=O)=O>O>[CH2:25]([CH:20]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:19][O:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)[CH3:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 317542(Cyclohex-1-en-1-yl)methanolHCID 1281542778016-72-5

Product 1

HCID 22222982HCID 22222982, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 mL round bottom flask equipped with a mechanical stirrer was charged with 33.6g (0.30 mol) cyclohexene-1-methanol, and 260 mL of DMSO. Sodium hydride (8.43 g, 95% in purity; 0.334 mol) was slowly added to above mixture in ice bath over 40 min. After the above mixture was reacted at room temperature for 2 hrs, the reaction mixture was warmed to room temperature. 2-Ethylhexyl tosylate (85.2 g, 0.30 mol) was slowly added to the above mixture over 15 min. The reaction was carried out for another 1 hr at room temperature, then 60° C. for 2 hrs. The reaction mixture was added to water (200 mL), and then extracted with chloroform (3×180 mL), washed with water (2×100 mL). The organic layer was evaporated and the residue distilled to give pure product.

Workup

  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. wait60° C. for 2 hrs
  4. extractionextracted with chloroform (3×180 mL)
  5. washwashed with water (2×100 mL)
  6. customThe organic layer was evaporated
  7. distillationthe residue distilled
  8. customto give pure product

Sources & evidence

ORD record
ord-83f299afd71047b082838fc89a04ea22
Source dataset
uspto-grants-2006_03
Patent number
US07018559B2

Reaction notes

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