Tetraethylene Glycol → Tetraethylene glycol mono-1-docosanyl ether

HRID 37762Notes

Reaction equation

HRID 37762 reaction equation
CS([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][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][CH2:26][CH3:27])(=O)=O.[CH2:28]([OH:40])[CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38]O.C(O[K])(C)(C)C>C(OCC)(=O)C>[CH2:6]([O:5][CH2:38][CH2:37][O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][OH:40])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][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][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8200Tetraethylene GlycolHCID 866500891-Docosanol, methanesulfonateHCID 178418922HCID 178418922, compound

Product 1

HCID 12572669Tetraethylene glycol mono-1-docosanyl ether

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

80.4 g of 1-docosanyl methanesulfonate was added to 207 mL of tetraethylene glycol, and the mixture was heated at 110° C. 40.0 g of t-butoxypotassium was gradually added over 2 hours. The mixture was further stirred for 3 hours, and after cooling, the reaction mixture was poured into 3 L of ice water, to which was then added 2 L of ethyl acetate, the mixture was stirred, and 22.2 g of an insoluble matter was filtered. An ethyl acetate phase was extracted and separated from the filtrate, after concentration under reduced pressure, 0.5 L of acetonitrile was added, and the mixture was stirred under ice cooling for one hour. The reaction mixture was filtered under reduced pressure and washed with 0.2 L of cold acetonitrile to obtain 81.6 g of a white crystal.

Workup

  1. temperatureafter cooling
  2. stirringthe mixture was stirred
  3. filtration22.2 g of an insoluble matter was filtered
  4. extractionAn ethyl acetate phase was extracted
  5. customseparated from the filtrate
  6. concentrationafter concentration under reduced pressure, 0.5 L of acetonitrile
  7. additionwas added
  8. stirringthe mixture was stirred under ice cooling for one hour
  9. filtrationThe reaction mixture was filtered under reduced pressure
  10. washwashed with 0.2 L of cold acetonitrile

Sources & evidence

ORD record
ord-5aca40845e4e4632b7d57f0e39ef7216
Source dataset
uspto-grants-2013_09
Patent number
US08524644B2

Reaction notes

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