Water → ({[1-(Hexadecyloxy)but-3-EN-2-YL]oxy}methyl)benzene

HRID 1199360Notes

Reaction equation

HRID 1199360 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([O:27][CH2:28][CH:29]([OH:32])[CH:30]=[CH2:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>CN(C)C=O>[CH2:11]([O:27][CH2:28][CH:29]([O:32][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:30]=[CH2:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 139590711-(Hexadecyloxy)but-3-EN-2-OL

Product 1

HCID 53992725({[1-(Hexadecyloxy)but-3-EN-2-YL]oxy}methyl)benzeneYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To stirred suspension of 3.35 g of 50% sodium hydride and 10.92 g of benzyl bromide in 75 ml of dimethylformamide was added a solution of 19 g of 1-(hexadecyloxy)-3-buten-2-ol in 75 ml of dimethylformamide. The mixture was stirred overnight, then water was added and the mixture was extracted with ether. The ether extract was dried over magnesium sulfate and activated charcoal and the solvent removed giving an oil. This oil was purified by HPLC [hexane: chloroform (8:1)] and the solvent removed giving 12 g of the desired compound as an oil.

Workup

  1. stirringThe mixture was stirred overnight
  2. extractionthe mixture was extracted with ether
  3. extractionThe ether extract
  4. dry with materialwas dried over magnesium sulfate and activated charcoal
  5. customthe solvent removed
  6. customgiving an oil
  7. customThis oil was purified by HPLC [hexane: chloroform (8:1)]
  8. customthe solvent removed

Sources & evidence

ORD record
ord-beb926c7b3384267931c357bc27c1f59
Source dataset
uspto-grants-1990_02
Patent number
US04900731

Reaction notes

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