4-Hydroxybenzoic Acid → 4-(4-Allyloxybutyloxy)benzoic acid

HRID 490033노트

반응식

HRID 490033 반응식
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8]Cl)[CH:2]=[CH2:3].[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH:2]=[CH2:3]

참가 물질

6

반응물 4

HCID 1354-Hydroxybenzoic AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 137481731-Chloro-4-[(prop-2-en-1-yl)oxy]butane

생성물 1

HCID 219606264-(4-Allyloxybutyloxy)benzoic acid수율 123%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A reaction mixture containing 14 g of allyl(4-chlorobutyl) ether, 14 g of 4-hydroxybenzoic acid, 14 g of potassium carbonate and 50 mL of dimethylformamide was stirred at 90° C. for 3 hours. Water was added to the reaction mixture, which was then extracted with toluene. The toluene layer was well washed with water, and then toluene was distilled off. 20 g of sodium hydroxide, 50 mL of water and 200 mL of ethanol were added to the resulting residue, followed by refluxing for 2 hours. Ethanol was distilled off, and hydrochloric acid was added to make the reaction mixture acidic. The mixture was extracted with diethyl ether and dried over anhydrous magnesium sulfate. A residue obtained by distilling the solvent was recrystallized from a mixed solvent of ethanol and water to obtain 29 g of 4-(4-allyloxybutyloxy)benzoic acid.

후처리

  1. extractionwas then extracted with toluene
  2. washThe toluene layer was well washed with water
  3. distillationtoluene was distilled off
  4. addition20 g of sodium hydroxide, 50 mL of water and 200 mL of ethanol were added to the resulting residue
  5. temperatureby refluxing for 2 hours
  6. distillationEthanol was distilled off
  7. additionhydrochloric acid was added
  8. extractionThe mixture was extracted with diethyl ether
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customA residue obtained
  11. distillationby distilling the solvent
  12. customwas recrystallized from a mixed solvent of ethanol and water

출처 및 근거

ORD 기록
ord-a0fdedeffaa44540bf2c29be6664c1cd
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07527746B2

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