Benzyl Alcohol → 1-Benzyl-3-(12-cyclohexyldodecyl)glycerine

HRID 231268ノート

反応式

HRID 231268 の反応式
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:11]1[CH:13]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:12]1.Cl>CS(C)=O.O1CCCC1>[CH2:3]([O:10][CH2:12][CH:13]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)[OH:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 148777861,2-Epoxy-3-(12-cyclohexyldodecyloxy)propane

生成物 1

HCID 539422351-Benzyl-3-(12-cyclohexyldodecyl)glycerine収率 78.9%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

In 100 ml of dimethylsulfoxide is suspended 1.4 g of sodium hydride, to which 9.73 g of benzyl alcohol is added dropwise at room temperature with stirring. After the addition is over, the mixture is gradually heated to 60° C. and stirred at that temperature for 40 minutes. Then, a solution of 9.7 g of 1,2-epoxy-3-(12-cyclohexyldodecyloxy)propane in 50 ml of tetrahydrofuran is added dropwise to the mixture and the resulting mixture is stirred at 60° C. for 2 hours. The thus obtaind reaction mixture is then neutralized with dilute hydrochloric acid and extracted with hexane-ethyl acetate (1:1). The extract layer is washed with water, dried and concentrated. The residue is purified by silica gel column chromatography to yield 10.2 g of the captioned compound as an oily substance.

後処理

  1. additionAfter the addition
  2. stirringstirred at that temperature for 40 minutes
  3. stirringthe resulting mixture is stirred at 60° C. for 2 hours
  4. customThe thus obtaind reaction mixture
  5. extractionextracted with hexane-ethyl acetate (1:1)
  6. washThe extract layer is washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-35128eac01ce49929cd511693933e352
出典データセット
uspto-grants-1989_07
特許番号
US04845219

反応ノート

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