Dimethyl Sulfoxide → Anisole, m-pentadecyl-

HRID 2276624

反応式

HRID 2276624 の反応式
CS(C)=O.[CH2:5]([C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[Na+].[CH3:29]I>O>[CH2:5]([C:20]1[CH:21]=[C:22]([O:26][CH3:29])[CH:23]=[CH:24][CH:25]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 68146Hydrogenated cardanol

生成物 1

HCID 578947Anisole, m-pentadecyl-収率 99.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Into a two-liter round bottomed flask was placed dimethyl sulfoxide (500 mL), 3-pentadecyl phenol (100.0 g, 0.33 mol) and sodium hydroxide (73.55 g, 1.31 mol). To this mixture methyl iodide (93.5 g, 0.66 mol) was added drop wise with stirring at room temperature. After the addition, the reaction mixture was stirred for further 6 h. Then the reaction mixture was poured into deionized water (1.5 liters). The organic material was extracted by addition of diethyl ether. The diethyl ether layer was separated, washed with water, dried over anhydrous sodium sulfate, and finally evaporated to afford the crude product as a viscous liquid. This material was purified by silica gel column chromatography using petroleum ether as the eluent to obtain 3-pentadecyl anisole Yield 104.6 g (97%), MP 27-28° C.

後処理

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for further 6 h
  3. extractionThe organic material was extracted by addition of diethyl ether
  4. customThe diethyl ether layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customfinally evaporated
  8. customto afford the crude product as a viscous liquid
  9. customThis material was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fc03ed5376cc44338cd3c06eb9cfab3a
出典データセット
uspto-grants-2015_09
特許番号
US09133089B2

関連ノート

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