Phenyl 4-methylbenzoate → HCID 53937160, compound

HRID 231658Notes

Reaction equation

HRID 231658 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])=[CH:3][CH:2]=1.[S]>CC(C)=O>[C:1]1([CH:16]=[CH:16][C:1]2[CH:2]=[CH:3][C:4]([C:7]([O:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:8])=[CH:5][CH:6]=2)[CH:6]=[CH:5][C:4]([C:7]([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 219444Phenyl 4-methylbenzoate2×HCID 5362487Sulfur

Product 1

HCID 53937160HCID 53937160, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
80 °C

Procedure

Sixty five g (0.306 mole) of neat phenyl p-toluate were maintained in the temperature range of 280°-310° C. (boiling point) while a slow stream of nitrogen was bubbled in from below the surface (sparged). Sulfur (1.92 g, 0.060 mole) dissolved in more phenyl p-toluate (20 g, 0.099 mole) at 100° C. was added slowly with stirring over a period of 2-3 hours. The heating, stirring and nitrogen sparging were continued an additional four hour and then the mixture was allowed to cool near 80° C. and 100 mL of boiling acetone was added. The suspension was transferred to a larger flask and an additional 400 mL of acetone was added. The suspension was filtered at the boil to yield 3.8 g of diphenyl 4,4'-stilbenedicarboxylate.

Workup

  1. customwas bubbled in from below the surface (sparged)
  2. additionwas added slowly
  3. stirringThe heating, stirring
  4. waitnitrogen sparging were continued an additional four hour
  5. customThe suspension was transferred to a larger flask
  6. filtrationThe suspension was filtered at the boil

Sources & evidence

ORD record
ord-3782f297a890490c9aa70b8bb2de398e
Source dataset
uspto-grants-1989_07
Patent number
US04847407

Reaction notes

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