p-Toluenesulfonic acid → Methyl 16-(2-tetrahydropyranyloxy)hexadecanoate

HRID 2258144

反応式

HRID 2258144 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].[C:21]1(C)C=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.C([O-])(O)=[O:33].[Na+]>ClCCl>[O:33]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 3496888Methyl 16-hydroxyhexadecanoate

生成物 1

HCID 12687990Methyl 16-(2-tetrahydropyranyloxy)hexadecanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

100.26 g (0.35 mol) of methyl 16-hydroxyhexadecanoate, 0.60 g (3.5 mol) of p-toluenesulfonic acid and 350 ml of dichloromethane were introduced into a 1-1 flask equipped with a stirrer and a dropping funnel and 32.39 g (0.385 mol) of dihydropyan was dropped thereto under stirring at 0° C. After the completion of the addition, the mixture was stirred at room temperature for additional 1 hour to thereby complete the reaction. Next, the reaction mixture was neutralized by adding 0.59 g (7 mmol) of NaHCO3 and filtered. After distilling off the solvent, crude methyl 16-(2-tetrahydropyranyloxy)hexadecanoate (III-a) was obtained.

後処理

  1. customequipped with a stirrer and a dropping funnel
  2. addition32.39 g (0.385 mol) of dihydropyan was dropped
  3. additionAfter the completion of the addition
  4. stirringthe mixture was stirred at room temperature for additional 1 hour
  5. customthe reaction
  6. filtrationfiltered
  7. distillationAfter distilling off the solvent

出典と根拠

ORDレコード
ord-b52d24b078eb4fa2883462d1a856be8a
出典データセット
uspto-grants-1997_08
特許番号
US05659052

関連ノート

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