Stearyl Alcohol → n-Octadecyl Sorbate

HRID 1594538ノート

反応式

HRID 1594538 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 22034995n-Octadecyl Sorbate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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═].

後処理

  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

出典と根拠

ORDレコード
ord-d4181062663045829912cc311a1e2401
出典データセット
uspto-grants-2001_09
特許番号
US06284258B1

反応ノート

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