p-Toluenesulfonic acid → HCID 67828174, compound

HRID 974219Notes

Reaction equation

HRID 974219 reaction equation
[C:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30]CC)=[O:29])=[CH:24][CH:23]=3)=[CH:18][CH:17]=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:1]([C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]\[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57129736HCID 57129736, compound

Product 1

HCID 67828174HCID 67828174, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

31.2 g of 1-(4-Carbo-tert.-butoxyphenyl)-2-(4'-carbethoxybiphenyl-4-yl)-ethene in 150 ml of absolute toluene are boiled under reflux for 3 hours with 1 g of p-toluene sulphonic acid. The reaction mixture is then evaporated to dryness, 8.68 g of NaOH in 100 ml of H2O and 100 ml of ethanol are added, and the mixture is boiled for 4 hours. It is then filtered hot after the addition of active charcoal, diluted with 200 ml of H2O and extracted twice with CH2Cl2, and the product is precipitated from the aqueous phase with conc. HCl.

Workup

  1. customThe reaction mixture is then evaporated to dryness, 8.68 g of NaOH in 100 ml of H2O and 100 ml of ethanol
  2. additionare added
  3. filtrationIt is then filtered hot
  4. additionafter the addition of active charcoal
  5. additiondiluted with 200 ml of H2O
  6. extractionextracted twice with CH2Cl2
  7. customthe product is precipitated from the aqueous phase with conc. HCl

Sources & evidence

ORD record
ord-3391d2e4954f4fea86dc6fcaf00f4879
Source dataset
uspto-grants-1991_11
Patent number
US05068300

Reaction notes

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