1,3-Propanediol → HCID 86759307、化合物

HRID 432972

反応式

HRID 432972 の反応式
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:21](O)[CH2:22][CH2:23][OH:24].[PH2](O)=O>>[C:1]([O:20][CH2:3][CH2:2][CH2:1][O:19][C:23](=[O:24])[CH2:22][CH2:21][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

4

反応物 3

HCID 104421,3-PropanediolHCID 4124402Phosphinic AcidHCID 5280933Gamma-Linolenic acid

生成物 1

HCID 86759307HCID 86759307、化合物

反応条件

温度
160 °C

実験手順

z,z,z-6,9,12-Octadecatrienoic acid (available from Sigma Chemicals) (0.180 mol, 50.0 g), propane-1,3-diol (0.086 mol, 6.5 g) and hypophosphorous acid (0.2 g) was heated with stirring to 160° C. under nitrogen. After 6 h, TLC (80:18:2 petroleum ether-ethyl ether-acetic acid) indicated that the reaction had gone to completion (Rf:0.56). The mixture was cooled down to room temperature and petroleum ether (700 mL) was added. The resulting solution was washed with saturated sodium bicarbonate (3×70 mL) and saturated sodium chloride (3×70 mL). It was then dried over anhydrous sodium sulphate and concentrated to dryness. Residual mono-ester and fatty acid were removed by distillation in vacuo (180° C., 10−2 mbar). The resulting oil was dissolved in petroleum ether to make up a 33% solution and was passed down a silica column. Hexane was finally removed to yield 1,3-di-(z,z,z-6,9,12-octadecatrienoyloxy)propane as a colourless oil.

後処理

  1. temperatureThe mixture was cooled down to room temperature
  2. washThe resulting solution was washed with saturated sodium bicarbonate (3×70 mL) and saturated sodium chloride (3×70 mL)
  3. dry with materialIt was then dried over anhydrous sodium sulphate
  4. concentrationconcentrated to dryness
  5. customResidual mono-ester and fatty acid were removed by distillation in vacuo (180° C., 10−2 mbar)
  6. dissolutionThe resulting oil was dissolved in petroleum ether
  7. customHexane was finally removed

出典と根拠

ORDレコード
ord-4966983d9fdf476783aaf4dd3fe37062
出典データセット
uspto-grants-2003_12
特許番号
US06664406B1

関連ノート

読み込み中…