Nitrobenzene → 4-[4-(Heptyloxy)phenyl]-4-oxobutanoic acid

HRID 1656873노트

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HRID 1656873 반응식
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[N+](C1C=CC=CC=1)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH2:8]([O:15][C:16]1[CH:17]=[CH:18][C:19]([C:4]([CH2:3][CH2:2][C:1]([OH:6])=[O:7])=[O:5])=[CH:20][CH:21]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

6

반응물 4

HCID 7416NitrobenzeneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) ChlorideHCID 11392287Benzene, (heptyloxy)-

생성물 1

HCID 28015934-[4-(Heptyloxy)phenyl]-4-oxobutanoic acid수율 75.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

Succinic anhydride (62.4 g) mashed by a mortar and pestle was placed in a 1 l three-necked flask, followed by adding heptyloxybenzene (100 g) and nitrobenzene (300 ml), portion-wise adding anhydrous aluminum chloride (150 g) under ice cooling, heating the mixture up to 50° C., agitating for 2 hours, allowing to stand overnight, after which the resulting reaction solution was poured in water, and subjected to steam distillation to distil off excess nitrobenzene, followed by ice-cooling, filtering off the resulting solids, heating under reflux together with toluene to remove water by means of Dien-Stark type drain tube, filtering off the solution while hot, recrystallizing from the filtrate, and further filtering off the resulting crystals, to obtain 3-(4-heptyloxybenzoyl)propionic acid (114.5 g). m.p.: 103.5°-105.7° C.

후처리

  1. customwas placed in a 1 l three-necked flask
  2. waitto stand overnight
  3. customafter which the resulting reaction solution
  4. distillationsubjected to steam distillation
  5. customto distil off excess nitrobenzene
  6. temperaturecooling
  7. filtrationfiltering off the resulting solids
  8. temperatureheating
  9. temperatureunder reflux together with toluene
  10. customto remove water by means of Dien-Stark type drain tube
  11. filtrationfiltering off the solution while hot,
  12. customrecrystallizing from the filtrate
  13. filtrationfurther filtering off the resulting crystals

출처 및 근거

ORD 기록
ord-e68403c0a2e74167a02ea896422f7494
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05256330

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