Water → 16-Sulfanylhexadecan-1-ol

HRID 1279136Notes

Reaction equation

HRID 1279136 reaction equation
[SH: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][C:17](O)=[O:18].CSC.B.O>C1COCC1>[SH: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][OH:18]

Participants

5

Reactant 3

HCID 962WaterHCID 352258516-Mercaptohexadecanoic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 376324616-Sulfanylhexadecan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

16-mercaptohexadecanoic acid (N) (0.2 g, 0.7 mmol) was dissolved in dry THF (20 mL) and borane dimethyl sulphide (1 mL, 1.1 equiv.) was slowly added under N2 atmosphere. The mixture was stirred at room temperature for 4 hr. Water was added to the solution was extracted using ethyl acetate. The organic extract was washed with 1N HCl, water and saturated sodium bicarbonate solution successively. After drying (MgSO4), the solvent was evaporated to give a white powder. Yield: 87 mg (46%)

Workup

  1. extractionwas extracted
  2. extractionThe organic extract
  3. washwas washed with 1N HCl, water and saturated sodium bicarbonate solution successively
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent was evaporated
  6. customto give a white powder

Sources & evidence

ORD record
ord-831901abc39b427182156db44a1dd0b0
Source dataset
uspto-grants-2002_09
Patent number
US06447656B1

Reaction notes

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