Dimethyl Sulfoxide → Anisole, m-pentadecyl-

HRID 2262870

반응식

HRID 2262870 반응식
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-].[K+].[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]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 68146Hydrogenated cardanol

생성물 1

HCID 578947Anisole, m-pentadecyl-수율 99.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Into a 2-liter round-bottomed flask was placed 500 milliliters (ml) of dimethyl sulfoxide, 100 grams (g) of 3-(n-pentadecyl)phenol (0.33 mol), and 73.55 g of potassium hydroxide (1.31 mol). To this mixture, 93.5 g of methyl iodide (0.66 mol) was added drop wise with stirring at room temperature. After the addition, the reaction mixture was stirred for a further 6 hours. 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 fluid. This material was purified by silica gel column chromatography using petroleum ether as the eluent to furnish 3-(n-pentadecyl)anisole (104.6 g, 97% of theoretical yield) having a melting range of 27-28° C.

후처리

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

출처 및 근거

ORD 기록
ord-0d450f2c81294154a40895a17af1580a
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851524B2

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