Triethylamine → 1-Docosanol, methanesulfonate

HRID 2284460Notes

Reaction equation

HRID 2284460 reaction equation
[CH2:1]([OH:23])[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)CC)C>O1CCCC1>[CH3:24][S:25]([O:23][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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12620Behenyl AlcoholHCID 31297Methanesulfonyl chloride

Product 1

HCID 866500891-Docosanol, methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

247.4 g of behenyl alcohol (1-docosanol) was dissolved in 640 mL of tetrahydrofuran, 116.1 mL of methanesulfonyl chloride was gradually added, and 64.7 mL of triethylamine was then added dropwise under ice cooling over 30 minutes. After stirring for one hour, the mixture was heated at 40° C. and further stirred for 30 minutes. The reaction mixture was poured into 3.5 L of ice water, and the resulting mixture was ultrasonically dispersed for 15 minutes and further stirred at room temperature for 4 hours. The dispersion was filtered under reduced pressure, and a crystal was washed with 2 L of water. The resulting white crystal was stirred in 1.5 L of acetonitrile for one hour, filtered under reduced pressure and then washed with 0.5 L of acetonitrile. The resulting crystal was dried under reduced pressure to obtain 303.4 g of a white crystal.

Workup

  1. stirringfurther stirred for 30 minutes
  2. additionthe resulting mixture was ultrasonically dispersed for 15 minutes
  3. stirringfurther stirred at room temperature for 4 hours
  4. filtrationThe dispersion was filtered under reduced pressure
  5. washa crystal was washed with 2 L of water
  6. stirringThe resulting white crystal was stirred in 1.5 L of acetonitrile for one hour
  7. filtrationfiltered under reduced pressure
  8. washwashed with 0.5 L of acetonitrile
  9. customThe resulting crystal was dried under reduced pressure

Sources & evidence

ORD record
ord-fc8dba8f6d8a441fa9d6889d44ee4d89
Source dataset
uspto-grants-2015_09
Patent number
US09145432B2

Reaction notes

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