1-Octanol → 2-Octyl glyceryl ether

HRID 1197383Notes

Reaction equation

HRID 1197383 reaction equation
S(=O)(=O)(O)O.[CH2:6]1[O:8][CH:7]1[CH2:9][OH:10].[OH-].[Na+].[CH2:13]([OH:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[CH2:13]([O:21][CH:7]([CH2:9][OH:10])[CH2:6][OH:8])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 4

HCID 9571-OctanolHCID 1118Sulfuric AcidHCID 11164GlycidolHCID 14798Sodium Hydroxide

Product 1

HCID 3724412-Octyl glyceryl etherYield 15.9%

Procedure

0.6 ml of concentrated sulfuric acid was added to 165 g of 1-octanol, the mixture was stirred at room temperature and 23.5 g of glycidol was added dropwise. The reaction mixture was poured on ice water, the mixture was neutralized with 1N aqueous sodium hydroxide solution and extracted with ether, and the ether layer was dried over anhydrous sodium sulfate. The solvent was distilled away, the most part of 1-octanol was removed by vacuum distillation, and the residue was distilled under a vacuum of 1 mmHg to give 10.3 g of the desired product containing a by-product 3-octyloxy-1,2-propanediol.

Workup

  1. additionThe reaction mixture was poured on ice water
  2. extractionextracted with ether
  3. dry with materialthe ether layer was dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away
  5. customthe most part of 1-octanol was removed by vacuum distillation
  6. distillationthe residue was distilled under a vacuum of 1 mmHg

Sources & evidence

ORD record
ord-77d767bd16c94fefa353489b0b82a92f
Source dataset
uspto-grants-1994_01
Patent number
US05275757

Reaction notes

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