Water → Methyl 2-butenyloxy-4-octyloxybenzoate

HRID 742525

반응식

HRID 742525 반응식
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:27](Br)=[CH:28][CH2:29][CH3:30].O>CC(=O)CC>[CH:27]([O:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[CH:28][CH2:29][CH3:30]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 359451-Bromobut-1-eneHCID 11536459Methyl 2-hydroxy-4-octyloxybenzoate

생성물 1

HCID 67738328Methyl 2-butenyloxy-4-octyloxybenzoate수율 89.9%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

To a solution of 22.0 g (78.5 mmol) of the compound (29) and 65.0 g (471 retool) of potassium carbonate mixed in 300 ml of 2-butanone were added 32.0 g (236 mmol) of butenyl bromide and the whole was refluxed for 18 hours. Water was added to the solution and the whole was extracted with ethyl acetate. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography to obtain 23.6 g of methyl 2-butenyloxy-4-octyloxybenzoate as a colorless clear liquid (yield: 89.9%). Then, 20.0 g (59.8 mmol) of the resulting compound was dissolved in 100 ml of methanol. The solution was poured into a solution of 12.0 g (300 mmol) of sodium hydroxide dissolved in 40 ml of water and 400 ml of methanol. The whole was refluxed for another 2 hours. After removal of the solvent by distillation, the resulting white solid was dissolved in water and the solution was rendered acidic by adding hydrochloric acid, whereby white precipitate formed. The precipitate was extracted with methylene chloride. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography to obtain 15.3 g of 2-butenyloxy-4-octyloxybenzoic acid (30) (yield: 80.0%).

후처리

  1. temperaturethe whole was refluxed for 18 hours
  2. extractionthe whole was extracted with ethyl acetate
  3. customAfter removal of the solvent
  4. distillationby distillation
  5. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3e707464077b474bb8d7e5c0ecfe2d46
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554706

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