1-Octadecanethiol → HCID 54014366, compound

HRID 2419506Notes

Reaction equation

HRID 2419506 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+].Br[C:23]([CH3:33])([CH3:32])[C:24]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:25]>C1C=CC=CC=1>[CH2:1]([S:19][C:23]([CH3:32])([CH3:33])[C:24]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:25])[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 10933510HCID 10933510, compound

Product 1

HCID 54014366HCID 54014366, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 14.3 g of stearylmercaptan and 200 ml of anhydrous benzene was heated with stirring, to which 1.2 g of sodium hydride was gradually added. To the reaction slurry in an ice bath, a solution containing 13.2 g of ethyl (2-bromo-2-methylpropionyl)acetate and 20 ml of anhydrous benzene was gradually added with stirring. After the completion of the addition, the reaction mixture was removed from the ice bath and stirred for three hours. The reaction mixture was then poured into ice water and neutralized by addition of glacial acetic acid. The mixture was extracted with 300 ml of ethyl acetate, the extract was washed twice with a saturated aqueous sodium chloride solution. The ethyl acetate phase was dried with anhydrous sodium carbonate. After distilling off the ethyl acetate, the residue was purified using silica gel chromatography (eluting solvent: chloroform) to obtain 16.2 g (yield 62%) of the intended compound having a melting point of 34° to 37° C.

Workup

  1. temperaturewas heated
  2. additionwas gradually added
  3. additionwas gradually added
  4. additionAfter the completion of the addition
  5. customthe reaction mixture was removed from the ice bath
  6. stirringstirred for three hours
  7. additionThe reaction mixture was then poured into ice water
  8. additionneutralized by addition of glacial acetic acid
  9. extractionThe mixture was extracted with 300 ml of ethyl acetate
  10. washthe extract was washed twice with a saturated aqueous sodium chloride solution
  11. dry with materialThe ethyl acetate phase was dried with anhydrous sodium carbonate
  12. distillationAfter distilling off the ethyl acetate
  13. customthe residue was purified
  14. washsilica gel chromatography (eluting solvent: chloroform)

Sources & evidence

ORD record
ord-d32b94ae56ee400a83630b4b86f2cb42
Source dataset
uspto-grants-1978_08
Patent number
US04106942

Reaction notes

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