Triethylamine → 2-Propenoic acid, 2-methyl-, (9Z)-9-octadecen-1-yl ester

HRID 566477

反応式

HRID 566477 の反応式
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20](Cl)(=[O:24])[C:21]([CH3:23])=[CH2:22].C(N(CC)CC)C>C(Cl)Cl>[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:24])[C:21]([CH3:23])=[CH2:22]

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 13528Methacryloyl chlorideHCID 5284499Oleyl Alcohol2 回

生成物 1

HCID 64363902-Propenoic acid, 2-methyl-, (9Z)-9-octadecen-1-yl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Oleyl alcohol (26.8 grams) is placed in a three-neck flask under a blanket of nitrogen. The entire reaction contents are cooled in an ice bath. Methacryloyl chloride (10.5 grams) dissolved in about 50 mL of methylene chloride is added slowly to the cooled oleyl alcohol with vigorous stirring in about 2 hours. Triethylamine (11.5 g) dissolved in 25 mL of methylene chloride is subsequently added in about an hour. After addition of triethylamine, the solution is allowed to warm to ambient temperature and is stirred for another 4 hours in order to complete the reaction. The precipitated triethylammonium chloride is removed by filtration, and the filtrate is washed with brine solution (saturated NaCl) followed by washings with dil. NaOH and dil. HCl. The organic layer is dried with anhydrous magnesium sulfate and the solvent is removed in vacuo to yield oleyl methacrylate in good yields. Oleyl methacrylate is stabilized from polymerization by addition of approximately 10 ppm hydroquinone. The structure of the product is verified by 1H and 13C NMR spectroscopy.

後処理

  1. customThe entire reaction contents
  2. temperatureare cooled in an ice bath
  3. additionis subsequently added in about an hour
  4. stirringis stirred for another 4 hours in order
  5. customthe reaction
  6. customThe precipitated triethylammonium chloride is removed by filtration
  7. washthe filtrate is washed with brine solution (saturated NaCl)
  8. washfollowed by washings with dil. NaOH and dil. HCl
  9. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  10. customthe solvent is removed in vacuo

出典と根拠

ORDレコード
ord-3892069c51ed44f78216608962b04d3e
出典データセット
uspto-grants-2001_01
特許番号
US06174948B1

関連ノート

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