Toluene → 4,4'-Bis(carbomethoxy)stilbene

HRID 5053

Reaction equation

HRID 5053 reaction equation
[Br-].[C:2]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)([O:4][CH3:5])=[O:3].[CH:32]([C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)=O.C1(C)C=CC=CC=1.C[O-].[Na+]>CO>[C:38]([C:37]1[CH:42]=[CH:43][C:34]([CH:32]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]([C:2]([O:4][CH3:5])=[O:3])=[CH:31][CH:30]=2)=[CH:35][CH:36]=1)([O:40][CH3:41])=[O:39]

Participants

6

Reactant 4

HCID 1140TolueneHCID 15294Methyl 4-FormylbenzoateHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 10942334Sodium Methoxide

Product 1

HCID 1391384,4'-Bis(carbomethoxy)stilbeneYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 126.35 g (251 mmol) (4-carbomethoxy)benzyltriphenylphosphonium bromide, 49.45 g (302 mmol) methyl 4-formylbenzoate, and 632 mL 2:1 methanol:toluene. After the starting material dissolved, 63.2 mL (277 mmol) 25% sodium methoxide solution in methanol was added dropwise over several minutes. The reaction vessel was heated at reflux for 30 minutes. After cooling to room temperature, the reaction vessel was cooled at 0° C. for several hours. The resulting precipitate was filtered and dried in a vacuum oven to afford 59.0 g (79%) 4,4'-bis(carbomethoxy)stilbene as a 7:3 mixture of cis:trans isomers.

Workup

  1. customTo a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum
  2. temperaturereflux condenser with a nitrogen inlet tube
  3. dissolutionAfter the starting material dissolved
  4. temperatureThe reaction vessel was heated
  5. temperatureat reflux for 30 minutes
  6. temperaturethe reaction vessel was cooled at 0° C. for several hours
  7. filtrationThe resulting precipitate was filtered
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-bdab6112829f4164810a4a13bdd2db90
Source dataset
uspto-grants-1993_09
Patent number
US05243021

Linked notes

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