Stearyl Alcohol → n-Octadecyl Sorbate

HRID 1594538

반응식

HRID 1594538 반응식
[C:1](Cl)(=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6].[CH2:9]([OH:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1COCC1>[C:1]([O:27][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])(=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6]

참가 물질

4

반응물 2

HCID 8221Stearyl AlcoholHCID 5368941(2E,4E)-hexa-2,4-dienoyl chloride

생성물 1

HCID 22034995n-Octadecyl Sorbate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 0.9 g (6.9 mmol) of sorboyl chloride in 6 mL of THF was added slowly with stirring to a mixture of 1.87 g (6.9 mmol) of n-octadecanol in 10 mL of THF at 40° C. The resulting mixture was refluxed for 16 hours. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel using chloroform as eluent. The appropriate fractions were combined and evaporated to dryness in vacuo to give a white solid product: 1.04 g (42%) yield. TLC (CHCl3)Rf=0.75. 1H NMR (300 MHz) δ 0.89 [3H, t, —(CH3)15CH3)],1.25 [30H, br m, —(CH3)15—], 1.62 [2H, t, —OCH2CH2—], 1.86 [3H, d, CH3CH═], 4.14 [2H, t, —OCH2—], 5.79 [1H, d, OCCH═], 6.19 [2H, m, CH3CH═CH—], 7.22 [1H, m, CH3CH═CH—CH═].

후처리

  1. temperatureThe resulting mixture was refluxed for 16 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe crude product was purified by column chromatography on silica gel
  4. customevaporated to dryness in vacuo
  5. customto give a white solid product
  6. custom1.04 g (42%) yield

출처 및 근거

ORD 기록
ord-d4181062663045829912cc311a1e2401
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06284258B1

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