Acetone → 1,3-Benzenedicarboxylic acid, diethyl ester
Reaction equation
BrCCCCCCOC1C=CC(C2C=CC(C#N)=CC=2)=CC=1.O[C:24]1[CH:25]=[C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:27]=[C:28]([CH:34]=1)[C:29]([O:31][CH2:32][CH3:33])=[O:30].CC(C)=O>O>[C:29]([O:31][CH2:32][CH3:33])(=[O:30])[C:28]1[CH:34]=[CH:24][CH:25]=[C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:27]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
0.08 mol (28.8 g) of 4-(6-bromohexyloxy)-4′-cyanobiphenyl, 0.08 mol (16.6 g) of diethyl 5-hydroxyisophthalate, 0.12 mol (19.2 g) of potassium carbonate anhydride and 400 ml of acetone were placed in a 1 l three-neck flask and the mixture was reacted under reflux for 24 hours by using a water bath. After the reaction solution was allowed to cool, it was poured into about 4 l of purified water to take out a precipitate, which was to be a crude subject product, by filtration and the precipitate was dried under reduced pressure (yield: 90% (37 g)). The resulting precipitate was recrystallized from acetone to obtain diethyl isophthalate carrying cyanobiphenyl through a hexyl group as a target product (yield: 73% (30 g)). The resulting compound was subjected to nuclear magnetic resonance (NMR) measurement. The results of measurement are shown below. Also, the compound was subjected to mass spectrometry, with the result that a peak corresponding to a molecular weight of 515.6 was confirmed.
Workup
- customthe mixture was reacted
- temperatureunder reflux for 24 hours
- temperatureto cool
- filtrationby filtration
- customthe precipitate was dried under reduced pressure (yield: 90% (37 g))
- customThe resulting precipitate was recrystallized from acetone
Sources & evidence
- ORD record
- ord-4b66bd81feb74d5f85c175b33f2e7d3a
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07501210B2
Reaction notes
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