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

HRID 1588365ノート

反応式

HRID 1588365 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].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:32]1[CH:37]=[CH:36][CH2:35][CH2:34][CH2:33]1.C([O-])(O)=O.[Na+]>ClCCl>[O:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]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

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 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 mmol) of p-toluenesulfonic acid and 350 ml of dichloromethane were introduced into a 1-l flask equipped with a stirrer and a dropping funnel. 32.39 g (0.385 mol) of dihydropyran was added dropwise thereto while stirring at 0° C. After the completion of the addition, the mixture was stirred at room temperature for an hour to thereby complete the reaction. Next, the reaction mixture was neutralized by adding 0.59 g (7 mmol) of NaHCO3. After filtering and removing solvent under reduced pressure; a crude product of methyl 16-(2-tetrahydropyranyloxy)hexadecanoate was obtained.

後処理

  1. customequipped with a stirrer and a dropping funnel
  2. additionAfter the completion of the addition
  3. stirringthe mixture was stirred at room temperature for an hour
  4. customthe reaction
  5. filtrationAfter filtering
  6. customremoving solvent under reduced pressure

出典と根拠

ORDレコード
ord-755174fab4794aadbf5f43ae93e007cd
出典データセット
uspto-grants-1993_06
特許番号
US05221757

反応ノート

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