Benzyl Alcohol → Benzene, [[(12-bromododecyl)oxy]methyl]-

HRID 2290809Notes

Reaction equation

HRID 2290809 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>O>[CH2:1]([O:8][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][Br:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 187661,12-DibromododecaneHCID 24758Sodium hydride

Product 1

HCID 11100339Benzene, [[(12-bromododecyl)oxy]methyl]-Yield 53.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2.16 g of benzyl alcohol and 30 ml of dimethylformamide was added 1.2 g of oily sodium hydride (60%). After stirring the mixture for 30 minutes at 20° to 25° C., 10 g of 1,12-dibromododecane was added to the mixture in one portion followed by stirring for 2 hours at 25° to 30° C. After the reaction was over, 300 ml of water was added to the reaction mixture and the product was extracted with n-hexane. The extract was washed with water, dried over anhydrous magnesium sulfate, and then, the solvent was distilled off. The oily residue was applied to silica gel column chromatography and eluted with a mixture of n-hexane and ether (9:1) to provide 3.8 g of 12-benzyloxy-1-bromododecane as an oily product.

Workup

  1. stirringby stirring for 2 hours at 25° to 30° C
  2. additionwas added to the reaction mixture
  3. extractionthe product was extracted with n-hexane
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. washeluted with a mixture of n-hexane and ether (9:1)

Sources & evidence

ORD record
ord-b2928c0f52f64c16b9afb9d78d0c6cbe
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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