Benzaldehyde → Methyl 4-(2-phenylethenyl)benzoate

HRID 2421624Notes

Reaction equation

HRID 2421624 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].[CH:38](=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1COCC1.O.C1(C)C=CC=CC=1>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([CH:2]=[CH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 11776TriphenylphosphineHCID 256687Methyl 4-(bromomethyl)benzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 53426079Methyl 4-(2-phenylethenyl)benzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(bromomethyl)benzoate (458 mg, 2 mmol) was added to dry toluene (8 mL) along with triphenylphosphine (609 mg, 2.2 mmol). Under nitrogen, reflux conditions were applied for three hours and the mixture was then permitted to cool to room temperature. The fine white solid was filtered off, washed thoroughly with EtOAc, and dried under vacuum (967 mg). This solid was stirred in dry THF (4 mL) under nitrogen, and potassium t-butoxide (246 mg, 2.18 mmol) was added. The bright orange mixture was heated under reflux for one hour. Upon cooling, benzaldehyde (202 μL, 212 mg, 1.2 mmol) in dry THF (2 mL) was added. Further heating under reflux was applied for thirty minutes. The reaction mixture was diluted with water and extracted with EtOAc. The organic layers were combined, washed with water and then brine, dried over MgSO4 and concentrated. The product was purified by flash chromatography on SiO2 using EtOAc/hexanes 10:90. A white solid was obtained (97 mg, 20%).

Workup

  1. temperatureUnder nitrogen, reflux conditions
  2. filtrationThe fine white solid was filtered off
  3. washwashed thoroughly with EtOAc
  4. customdried under vacuum (967 mg)
  5. temperatureThe bright orange mixture was heated
  6. temperatureunder reflux for one hour
  7. temperatureUpon cooling
  8. temperatureFurther heating
  9. temperatureunder reflux
  10. waitwas applied for thirty minutes
  11. extractionextracted with EtOAc
  12. washwashed with water
  13. dry with materialbrine, dried over MgSO4
  14. concentrationconcentrated
  15. customThe product was purified by flash chromatography on SiO2
  16. customA white solid was obtained (97 mg, 20%)

Sources & evidence

ORD record
ord-55c2636eee7d40269b3a70ce0272c7d8
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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