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

HRID 864278노트

반응식

HRID 864278 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8900Heptane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c842d7bca0a4034819f2cfce75972f4
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563038

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