Benzoyl Peroxide → 7-Thia-tetradecan-5-ene-1-ol

HRID 356802Notes

Reaction equation

HRID 356802 reaction equation
[CH2:1]([SH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:9]([OH:15])[CH2:10][CH2:11][CH2:12][C:13]#[CH:14].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CCCCCCC>[CH2:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH:13]=[CH:14][S:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 154221-HeptanethiolHCID 702345-Hexyn-1-olHCID 516892Sodium Bicarbonate

Product 1

HCID 536439997-Thia-tetradecan-5-ene-1-olYield 30%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

To 1.332 gr (10 mmol) of n-heptyl mercaptan and 981 mg (10 mmol) of 5-hexyn-1-ol dissolved in 25 ml of heptane under an argon atmosphere was added a few crystals of dibenzoyl peroxide. The reaction was stirred magnetically and heated to reflux for 18 hours. It was then cooled and poured into 25 ml of 10% sodium bicarbonate and extracted with 3×25 ml of ethyl acetate. The organic phases were combined and dried over sodium sulfate, filtered, and evaporated to yield a yellow oil. The oil was chromatographed on eight silica gel type GF preparative plates, using hexane-ethyl acetate (4:1) as developing solvent. Following removal of the band corresponding to product from the plates, the product was extracted from the silica with methanol, 684 mg (30% yield) of pure 7-thia-tetradecan-5-ene-1-ol was obtained as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. temperatureIt was then cooled
  4. extractionextracted with 3×25 ml of ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a yellow oil
  9. customThe oil was chromatographed on eight silica gel type GF preparative plates
  10. customremoval of the band corresponding to product from the plates
  11. extractionthe product was extracted from the silica with methanol

Sources & evidence

ORD record
ord-1f0cc94f655e4e0da4f7dfd568e2cffc
Source dataset
uspto-grants-1998_11
Patent number
US05840508

Reaction notes

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