1-Dodecanethiol → HCID 178442864, compound

HRID 634603Notes

Reaction equation

HRID 634603 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=O.[CH2:15]([SH:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C[O-:29].[Na+]>CO>[CH2:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:15]([OH:29])=[S:27])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH3:2]

Participants

5

Reactant 3

HCID 81951-DodecanethiolHCID 1781211-Bromoundecanoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 178442864HCID 178442864, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 1000 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube were charged 26.6 g of 11-bromoundecanoic acid, 21.2 g of 1-dodecanthiol, 42.4 ml of sodium methoxide (28% methanol solution) and 300 ml of methanol, and the mixture was refluxed for 6 hours on an oil bath. After cooling the reaction mixture to room temperature, the precipitated crystals were collected by filtration under reduced pressure and washed with methanol. The resulting crystals were suspended in 1000 ml of distilled water, and the suspension was made pH 2 by adding a conc. hydrochloric acid, and suspension was stirred on an oil bath at 60° C. for 30 minutes to carry out neutraliza tion. Crystals after neutralization were collected by filtration under reduced pressure and washed with distilled water. The residue was recrystallized from ethanol to obtain 35.2 g of the title compound.

Workup

  1. customIn a 1000 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube
  2. temperaturethe mixture was refluxed for 6 hours on an oil bath
  3. filtrationthe precipitated crystals were collected by filtration under reduced pressure
  4. washwashed with methanol
  5. additionby adding a conc. hydrochloric acid, and suspension
  6. filtrationCrystals after neutralization were collected by filtration under reduced pressure
  7. washwashed with distilled water
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-64b56bd13e744699b6337f1002798bf9
Source dataset
uspto-grants-2001_02
Patent number
US06184180B2

Reaction notes

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