p-Toluenesulfonic acid → 4,4'-cis-Stilbenedicarboxylic acid

HRID 974212Notes

Reaction equation

HRID 974212 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]\[C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24]C(C)(C)C)=[O:23])=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)=[O:7])(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:11]1(/[CH:14]=[CH:15]\[C:16]2[CH:17]=[CH:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][CH:21]=2)[CH:10]=[CH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67931836Z-4,4'-Stilbene-dicarboxylic acid di-tert.-butyl ester

Product 1

HCID 186479614,4'-cis-Stilbenedicarboxylic acidYield 98.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

331 g of Z-4,4'-Stilbene-dicarboxylic acid di-tert.-butyl ester in 1700 ml of absolute toluene are boiled under reflux for 3 hours together with 10.3 g of p-toluene sulphonic acid. The reaction mixture is then concentrated by evaporation and boiled under reflux for 4 hours with 104.2 g of NaOH, 1300 ml of H2O and 1300 ml of ethanol. The reaction mixture is filtered hot after the addition of active charcoal, diluted with about 3 l of H2O and extracted twice, in each case with 1 l of CH2Cl2. Concentrated HCl is then added to the aqueous phase. 230 g of Z-4,4'-stilbene dicarboxylic acid are obtained after suction filtration and drying.

Workup

  1. concentrationThe reaction mixture is then concentrated by evaporation
  2. temperatureunder reflux for 4 hours with 104.2 g of NaOH, 1300 ml of H2O and 1300 ml of ethanol
  3. filtrationThe reaction mixture is filtered hot
  4. additionafter the addition of active charcoal
  5. additiondiluted with about 3 l of H2O
  6. extractionextracted twice, in each case with 1 l of CH2Cl2
  7. additionConcentrated HCl is then added to the aqueous phase

Sources & evidence

ORD record
ord-5f56900e07bf40a0a9b685b8dd30f335
Source dataset
uspto-grants-1991_11
Patent number
US05068300

Reaction notes

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