Salicylaldehyde → 2-Undecyloxybenzaldehyde

HRID 568899

반응식

HRID 568899 반응식
[H-].[Na+].[CH:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CN(C)C=O.CCCCCC>[CH2:22]([O:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[CH:3]=[O:11])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

참가 물질

6

반응물 3

HCID 6998SalicylaldehydeHCID 127441-BromoundecaneHCID 24758Sodium hydride

생성물 1

HCID 156174952-Undecyloxybenzaldehyde

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8058Hexane용매

실험 절차

To a stirred suspension of sodium hydride (10.0 mmoles), which was prewashed with petroleum ether, in sieve dried dimethylformamide (10 ml) was added dropwise a solution of salicylaldehyde (10.1 mmoles) in dimethylformamide (1 ml). To the reaction mixture was then added undecyl bromide (10.0 mmoles) and the mixture stirred for 16 hours at ambient temperature under nitrogen. The reaction mixture was taken up in hexane (50 ml) and washed with 10 percent sodium hydroxide (2×50 ml) and saturated sodium chloride (50 ml). The organic phase was dried over anhydrous magnesium sulfate and charcoal. Evaporation of the volatiles yielded a colorless liquid which was purified by flash chromatography over silica gel with 2 percent ethyl acetate in hexane as eluant to afford the desired product as an oil.

후처리

  1. washwashed with 10 percent sodium hydroxide (2×50 ml) and saturated sodium chloride (50 ml)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate and charcoal
  3. customEvaporation of the volatiles
  4. customyielded a colorless liquid which
  5. customwas purified by flash chromatography over silica gel with 2 percent ethyl acetate in hexane as eluant

출처 및 근거

ORD 기록
ord-b8010cf9df3547c28754e3a851c51719
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04730005

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