p-Toluenesulfonic acid → Z,E-1,4-Bis-(4-carboxy-styryl)-benzene

HRID 974217Notes

Reaction equation

HRID 974217 reaction equation
[C:1]([C:8]1[CH:36]=[CH:35][C:11](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]\[C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30]C(C)(C)C)=[O:29])=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([O:3]C(C)(C)C)=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:28]([C:25]1[CH:24]=[CH:23][C:22](/[CH:21]=[CH:20]/[C:17]2[CH:18]=[CH:19][C:14](/[CH:13]=[CH:12]\[C:11]3[CH:35]=[CH:36][C:8]([C:1]([OH:3])=[O:2])=[CH:9][CH:10]=3)=[CH:15][CH:16]=2)=[CH:27][CH:26]=1)([OH:30])=[O:29]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67828321Z,E-1,4-Bis-(4-carbo-tert.-butoxy-styryl)benzene

Product 1

HCID 67828586Z,E-1,4-Bis-(4-carboxy-styryl)-benzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

131 g of Z,E-1,4-Bis-(4-carbo-tert.-butoxy-styryl)benzene are boiled under reflux with 6.5 g of p-toluenesulphonic acid in 1 l of toluene for 3 hours. The reaction product is evaporated to dryness and heated for a further 4 hours with 30 g of NaOH in 300 ml of water and 600 ml of ethanol. The ethanol is distilled off and the residue is acidified (conc. HCl) after dilution with water. The product is suction filtered and dried.

Workup

  1. customThe reaction product is evaporated to dryness
  2. temperatureheated for a further 4 hours with 30 g of NaOH in 300 ml of water and 600 ml of ethanol
  3. distillationThe ethanol is distilled off
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-599b23970bfd45388bcf042611b86e8e
Source dataset
uspto-grants-1991_11
Patent number
US05068300

Reaction notes

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