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

HRID 1656873Notes

Reaction equation

HRID 1656873 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e68403c0a2e74167a02ea896422f7494
Source dataset
uspto-grants-1993_10
Patent number
US05256330

Reaction notes

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