Benzyl Chloride → 1-Benzyloxy-3-hexadecyloxy-2-butanol

HRID 2081516Notes

Reaction equation

HRID 2081516 reaction equation
[CH2:1]([O:17][CH:18]([CH3:23])[CH:19]([OH:22])[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[H-].[Na+].[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH2:26]([O:21][CH2:20][CH:19]([OH:22])[CH:18]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:23])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 142331613-Hexadecyloxybutane-1,2-diol

Product 1

HCID 150522931-Benzyloxy-3-hexadecyloxy-2-butanolYield 19.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 100 ml of dry dimethylformamide, 17.67 g of 3-hexadecyloxybutane-1,2-diol was treated with 2.36 g of 60% sodium hydride under chilling with ice. To the chilled mixture was added 6.77 g of benzyl chloride, and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was recovered in a conventional manner and purified by silica gel column chromatography to give 4.33 g of 1-benzyloxy-3-hexadecyloxy-2-butanol.

Workup

  1. temperatureunder chilling with ice
  2. customThe reaction mixture was recovered in a conventional manner
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9ccfcdb4c22d4fba9b2797ab4f2f7125
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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