Toluene → 1,1-bis(4-methoxyphenyl)ethylene

HRID 1770335Notes

Reaction equation

HRID 1770335 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=O)=[CH:5][CH:4]=1.[C:19]1(C)C=CC=CC=1.C[Mg]Br.[Cl-].[NH4+]>O.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH2:19])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 70324,4'-DimethoxybenzophenoneHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 3167241,1-bis(4-methoxyphenyl)ethylene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 258 g 4,4'-dimethoxybenzophenone in 3000 ml warm toluene was added to 1600 ml 1.4M methylmagnesium bromide under nitrogen with stirring, over a one-hour period. The reaction temperature was kept below 40° C. After addition was complete, stirring was continued for one hour at 30°-40° C. and two hours at 50° C. The mixture was cooled to room temperature and poured into a stirred mixture of 400 ml acetic acid and 624 g ammonium chloride in 7200 ml deionized water. After gas evolution and exotherm had subsided, the organic (toluene) phase was separated and the aqueous phase was washed with 2×600 ml toluene. The combined toluene phases were washed with 1×2400 ml water, then placed in a flask and treated with a solution of 1470 ml deionized water and 1470 ml acetic acid at 50° C. for three hours to effect dehydration of the intermediate hydroxy compound. On cooling, the phases were separated and the toluene phase was washed with 2×1000 ml deionized water, then dried over magnesium sulfate. Filtration and removal of toluene gave a slightly wet cake which was triturated with 1400 ml diethyl ether, filtered and dried to give 222 g 1,1-di(p-methoxyphenyl)-ethene, m.p. 141°-143° C. whose structure was also confirmed by NMR.

Workup

  1. customwas kept below 40° C
  2. additionAfter addition
  3. stirringstirring
  4. customthe organic (toluene) phase was separated
  5. washthe aqueous phase was washed with 2×600 ml toluene
  6. washThe combined toluene phases were washed with 1×2400 ml water
  7. customplaced in a flask
  8. additiontreated with a solution of 1470 ml
  9. customat 50° C.
  10. customfor three hours
  11. temperatureOn cooling
  12. customthe phases were separated
  13. washthe toluene phase was washed with 2×1000 ml
  14. dry with materialdried over magnesium sulfate
  15. filtrationFiltration and removal of toluene
  16. customgave a slightly wet cake which
  17. customwas triturated with 1400 ml diethyl ether
  18. filtrationfiltered
  19. customdried

Sources & evidence

ORD record
ord-e57f608508a6460e96af8e13a8d598b4
Source dataset
uspto-grants-1995_01
Patent number
US05386058

Reaction notes

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