Ethyl Acetate → 2,2'-(Decane-1,10-diyldisulfanediyl)di(propan-1-ol)

HRID 2072223Notes

Reaction equation

HRID 2072223 reaction equation
[CH3:1][CH:2]([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17][CH:18]([CH3:22])[C:19](O)=[O:20])[C:3](O)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C>O1CCCC1>[CH3:22][CH:18]([S:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][S:6][CH:2]([CH3:1])[CH2:3][OH:4])[CH2:19][OH:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3383722,2'-(Decane-1,10-diyldisulfanediyl)dipropanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 213180912,2'-(Decane-1,10-diyldisulfanediyl)di(propan-1-ol)Yield 83.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution in tetrahydrofuran of 7 g (0.0200 mole) of (±)-2,15-dimethyl-3,14-dithia-1,16-hexadecanedioic acid was slowly poured under a current of nitrogen into an agitated suspension of 2.3 g (0.0605 mole) of LiAlH4 in tetrahydrofuran. The reaction medium was then heated under reflux for 3 hours 15 mins. After neutralisation of the excess reducing agent with ethyl acetate and aqueous alkali, the reaction mixture was filtered and then the solvents were eliminated from the filtrate. The residue was separated between water and methylene chloride. The organic phase was recovered and then washed to neutrality and dried. The solvent was evaporated under reduced pressure and the residue was washed by trituration with petroleum ether. After filtration, 5.4 g of a white crystalline powder was obtained which was insoluble in water. (H is understood that the (+) and (-) isomers can be separated from the racemic form by known methods).

Workup

  1. temperatureThe reaction medium was then heated
  2. temperatureunder reflux for 3 hours 15 mins
  3. filtrationthe reaction mixture was filtered
  4. customThe residue was separated between water and methylene chloride
  5. customThe organic phase was recovered
  6. washwashed to neutrality
  7. customdried
  8. customThe solvent was evaporated under reduced pressure
  9. washthe residue was washed by trituration with petroleum ether
  10. filtrationAfter filtration

Sources & evidence

ORD record
ord-d65467f4a6934361bd180c4197d37ecb
Source dataset
uspto-grants-1977_09
Patent number
US04049829

Reaction notes

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