Ethanol → 1-Tetradecyl-3-ethylglycerol

HRID 2091489

Reaction equation

HRID 2091489 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].C(O)C.[CH2:8]([O: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])[CH:9]1[O:11][CH2:10]1>>[CH2:13]([O:12][CH2:8][CH:9]([CH2:10][O:1][CH2:2][CH3:3])[OH:11])[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

4

Reactant 3

HCID 702EthanolHCID 38190Oxirane, 2-((tetradecyloxy)methyl)-HCID 2723922Sodium ethoxide

Product 1

HCID 866529161-Tetradecyl-3-ethylglycerolYield 319.6%

Conditions

Temperature
80 °C

Procedure

Under nitrogen stream, 30 g of sodium ethoxide was added to 851.8 g (18.5 mol) of ethanol, and the mixture was heated to 80° C. Then, 500 g (1.85 mol) of tetradecyl glycidyl ether were added dropwise thereto. The mixture was stirred for 18 hours at the same temperature. Thereafter, ethanol was distilled off, and 10.8 g of 85% phosphoric acid was added thereto, followed by washing the resultant mixture with water three times. After water washing, distillation was performed under reduced pressure, to thereby obtain 446 g of 1-tetradecyl-3-ethylglycerol (yield 76.2%).

Workup

  1. distillationThereafter, ethanol was distilled off
  2. addition10.8 g of 85% phosphoric acid was added
  3. washby washing the resultant mixture with water three times
  4. distillationAfter water washing, distillation

Sources & evidence

ORD record
ord-7de36ed9740c418595431acf70cab376
Source dataset
uspto-grants-2013_05
Patent number
US08440645B2

Linked notes

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