1-Iodohexadecane → 2-(Benzyloxy)-3-(hexadecyloxy)propan-1-ol

HRID 235697

反応式

HRID 235697 の反応式
[H-].[Na+].[CH2:3]([O:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:16](I)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CN(C)C=O>[CH2:31]([O:15][CH2:14][CH:11]([O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:12][OH:13])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16]

参加物

5

反応物 3

HCID 110071-IodohexadecaneHCID 24758Sodium hydrideHCID 2035672-(Phenylmethoxy)-1,3-propanediol

生成物 1

HCID 132771402-(Benzyloxy)-3-(hexadecyloxy)propan-1-ol収率 26.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a suspension of about 14.26 g of washed about 50% sodium hydride in about 500 ml of dimethylformamide was added about 49.2 g of 2-(benzyloxy)-1,3-propanediol over about 20 minutes. The mixture was stirred for about 40 minutes, then cooled to about 0° C. and about 95.13 g of hexadecyl iodide were added. After standing about 10 minutes, the mixture was stirred at room temperature for about 3 hours, then filtered through celite and diluted with about 1000 ml of water. This mixture was extracted with petroleum ether. The ether extract was dried and the solvent removed giving an oil. This oil was chromatographed on a column of florisil, eluting first with petroleum ether and then successively with about 5% and about 10% ether in petroleum ether to elute the product, giving about 28.8 g of the desired title compound as a light yellow oil.

後処理

  1. waitAfter standing about 10 minutes
  2. stirringthe mixture was stirred at room temperature for about 3 hours
  3. filtrationfiltered through celite
  4. additiondiluted with about 1000 ml of water
  5. extractionThis mixture was extracted with petroleum ether
  6. extractionThe ether extract
  7. customwas dried
  8. customthe solvent removed
  9. customgiving an oil
  10. customThis oil was chromatographed on a column of florisil
  11. washeluting first with petroleum ether
  12. washsuccessively with about 5% and about 10% ether in petroleum ether to elute the product

出典と根拠

ORDレコード
ord-a4eda06d550a4181ae7848f8b6d71f42
出典データセット
uspto-grants-1987_02
特許番号
US04640913

関連ノート

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