1-Octadecanethiol → 3,6,9,12,15,18,21,24-Octaoxa-27-thiapentatetracontan-1-ol

HRID 261344Notes

Reaction equation

HRID 261344 reaction equation
[CH2:1]([SH:19])[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][CH3:18].[H-].[Na+].S(O[CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][OH:59])(C1C=CC(C)=CC=1)(=O)=O>COCCOC>[CH2:58]([OH:59])[CH2:57][O:56][CH2:55][CH2:54][O:53][CH2:52][CH2:51][O:50][CH2:49][CH2:48][O:47][CH2:46][CH2:45][O:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39][O:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][S:19][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][CH3:18]

Participants

5

Reactant 3

HCID 179051-OctadecanethiolHCID 24758Sodium hydrideHCID 20394899PEG10-Tos

Product 1

HCID 203948883,6,9,12,15,18,21,24-Octaoxa-27-thiapentatetracontan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
85 °C

Procedure

To a heated (40° C.) solution of 20.1 g (0.97 mole) of n-octadecanethiol in 200 ml of dried 1.2-dimethoxyethane was slowly added under argon 0.07 mole (3.4 g., 50%) of sodium hydride (rinsed with hexane to remove the mineral oil) slurried in 1,2-dimethoxyethane. The reaction mixture was then heated at reflux (85° C.) with stirring for 2 hrs. A solution of 40 g. (0.07 mole) of the nonaethylene glycol monotosylate in 200 ml. 1,2-dimethoxyethane was added dropwise and the reaction mixture allowed to reflux with stirring for 16 hours. The mixture was cooled, insoluble salts were filtered, and the solvent was evaporated to yield a near quantitative yield (0.07 mole) of the thioether.

Workup

  1. washrinsed with hexane
  2. customto remove the mineral oil)
  3. temperatureThe reaction mixture was then heated
  4. temperatureto reflux
  5. stirringwith stirring for 16 hours
  6. temperatureThe mixture was cooled
  7. filtrationinsoluble salts were filtered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-33a73f430b8547979ee140dbbcc1bcdd
Source dataset
uspto-grants-1979_08
Patent number
US04165334

Reaction notes

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