Sodium Iodide → Di-n-decyl ether

HRID 2298786Notes

Reaction equation

HRID 2298786 reaction equation
[H-].[Na+].[Na+].[I-].[CH2:5]([OH:9])[CH2:6][CH2:7]O.[H][H].[CH2:12](Cl)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CN(C=O)C.O>[CH2:12]([O:9][CH2:5][CH2:6][CH2:7][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 104421,3-PropanediolHCID 138481-ChlorodecaneHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 17152Di-n-decyl ether

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of NaH (2.6 g, 70 mmol) and anhydrous NaI (9.9 g, 70 mmol) in dry DMF (80 mL) under N2 was added dropwise a solution of 1,3-propanediol (4.75 mL, 70 mmol) in DMF (20 mL). The mixture was stirred until hydrogen evolution had ceased, decyl chloride (1.34 g, 7.6 mmol) was added and stirring was continued at 50° C. for 18 hours. Then, the reaction mixture was poured into H2O (300 mL) and extracted with diethyl ether (3×250 mL). The organic extracts were combined, washed with sat. NaCl (100 mL), dried (MgSO4) and evaporated to dryness. The residue was subjected to silica-gel column chromatography [eluent: ethyl acetate/hexane, 30/70, v/v] to furnish decyl ether Compound 17 as a colourless oil.

Workup

  1. extractionextracted with diethyl ether (3×250 mL)
  2. washwashed with sat. NaCl (100 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-636c22d6e1c1429b88dbee534f3a1166
Source dataset
uspto-grants-2002_12
Patent number
US06495532B1

Reaction notes

Loading…