Dimethyl Sulfoxide → 3-Benzoxymethylcyclohexene

HRID 1744714Notes

Reaction equation

HRID 1744714 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+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:7]([O:8][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 317542(Cyclohex-1-en-1-yl)methanol

Product 1

HCID 157413843-Benzoxymethylcyclohexene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 mL round bottom flask equipped with a mechanical stirrer was charged with 19.8 g (0.177 mol) cyclohexene-1-methanol, and 150 mL of DMSO. Sodium hydride (4.90 g, 95% in purity; 0.194 mol) was slowly added to above mixture in an ice bath over 20 min. After the above mixture was reacted at room temperature for 1 hr, 30.2 g (0.177 mol) of benzylbromide was slowly added to the above mixture over 15 min. The reaction was carried out at 60° C. for 2 hrs. The reaction mixture was cooled to room temperature and was added to water (200 mL), and then extracted with chloroform (3×200 mL), washed with water (2×250 mL) and dried with sodium sulfate. The solvent 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 1 hr
  3. extractionextracted with chloroform (3×200 mL)
  4. washwashed with water (2×250 mL)
  5. dry with materialdried with sodium sulfate
  6. customThe solvent was evaporated
  7. distillationthe residue distilled
  8. customto give pure product

Sources & evidence

ORD record
ord-9d9c12228ff740e2bd329e6473d7c7e6
Source dataset
uspto-grants-2006_03
Patent number
US07018559B2

Reaction notes

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