Dimethyl Sulfoxide → 6-Methyl-3-hexoxymethylcyclohexene

HRID 1744725ノート

反応式

HRID 1744725 の反応式
C[CH:2]1[CH:7]([CH2:8][OH:9])[CH2:6][CH:5]=[CH:4][CH2:3]1.[CH3:10]S(C)=O.[H-].[Na+].[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O>[CH3:10][CH:4]1[CH:3]=[CH:2][CH:7]([CH2:8][O:9][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:6][CH2:5]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 1106373-Cyclohexene-1-methanol, 6-methyl-

生成物 1

HCID 222229906-Methyl-3-hexoxymethylcyclohexene

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 500 mL round bottom flask equipped with a mechanical stirrer was charged with 18.9g (0.15 mol) 6-methyl-3-cyclohexenemethanol, and 130 mL of DMSO. Sodium hydride (4.22 g, 95% in purity; 0.167 mol) was slowly added to above mixture in ice bath over 25 min. After the above mixture was reacted at room temperature for 2 hrs. Hexyl bromide (27.3 g, 0.165 mol) was slowly added to the above mixture over 25 min. The reaction was carried at room temperature for 1 hr, then 70° C overnight. The reaction mixture was added to water (150 mL), and then extracted with chloroform (3×150 mL), washed with water (2×150 mL), dried with sodium sulfate. The solvent was evaporated and the residue distilled to give pure product.

後処理

  1. customA 500 mL round bottom flask equipped with a mechanical stirrer
  2. customAfter the above mixture was reacted at room temperature for 2 hrs
  3. custom70° C overnight
  4. extractionextracted with chloroform (3×150 mL)
  5. washwashed with water (2×150 mL)
  6. dry with materialdried with sodium sulfate
  7. customThe solvent was evaporated
  8. distillationthe residue distilled
  9. customto give pure product

出典と根拠

ORDレコード
ord-b1efc1c3bb5b424ba5850d9b2a0e068e
出典データセット
uspto-grants-2006_03
特許番号
US07018559B2

反応ノート

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