1-Dodecanethiol → 1-Propanol, 3-(dodecylthio)-

HRID 617866Notes

Reaction equation

HRID 617866 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][SH:13].[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][OH:20]>CN(C)C=O>[CH2:12]([S:13][CH2:17][CH2:18][CH2:19][OH:20])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 81951-DodecanethiolHCID 123083-Bromo-1-propanolHCID 24758Sodium hydride

Product 1

HCID 41722041-Propanol, 3-(dodecylthio)-Yield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Dodecylthiol (5 g) was dissolved in 50 ml of dry N,N-dimethylformamide and 1 g of 60% sodium hydride was added thereto under ice-cooling. The mixture was stirred at room temperature for 1 hour. Further, a solution of 3.45 g of 3-bromopropanol in 10 ml of dry N,N-dimethylformamide was dropwise added thereto under ice-cooling and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice, extracted with ether and washed with 1N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution. The ether layer was dehydrated and concentrated. The resultant mixture was purified by silica gel column chromatography using hexane-ethyl acetate (10:1→3:1) as an eluent to give 6.071 g of 3-dodecylthiopropanol as a colorless powder.

Workup

  1. temperatureunder ice-cooling
  2. temperatureunder ice-cooling
  3. stirringthe mixture was stirred at room temperature for 3 hours
  4. additionThe reaction mixture was poured into ice
  5. extractionextracted with ether
  6. washwashed with 1N hydrochloric acid
  7. concentrationconcentrated
  8. customThe resultant mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d7c4fcb2c6a54f039a510fab21f4d540
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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