Hydrochloric Acid → Cinnamoylbenzene

HRID 742084Notes

Reaction equation

HRID 742084 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]1([C:19]2C=CC=CC=2)[CH:16]=[CH:15][C:14](C=O)=[CH:13][CH:12]=1.[OH-].[Na+].Cl>C(O)C.O>[C:11]1([CH:19]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68490alpha-HydroxyacetophenoneHCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Product 1

HCID 7189CinnamoylbenzeneYield 33%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4.92 g (36.1 mmol) of 2-hydroxyacetophenone, 3.30 g (34.2 mmol) of ,4'-(α-methyl)ethenyl, biphenyl 4-carboxaldehyde and 8.15 g NaOH (in 15 ml of water) in 100 ml of ethanol was stirred for 12 hours before the solution was poured into 400 ml of water. The resulting mixture was neutralized with dilute HCl to yield a chalcone. The yellow precipitate obtained was filtered and dried. The chalcone was purified by recrystallized from methylene chloride. Further oxidation of above chalcone was carried out with excess of H2O2 (30%) in ethanol under basic conditions for 12 hours. The resulting solution was poured into 500 ml water and acidified with dilute HCl. Yellow precipitate obtained was filtered and dried. Product was recrystallized form THF/hexane mixture. Yield: 33%. Quantum Yield: (1.8 relative to 3HF in methyl cyclohexane), Extinction coefficient: εmax (M-1 cm-1)=36000. λmax (abs)=355 nm and λmax (em )=550 nm.

Sources & evidence

ORD record
ord-2f15d7c56b7041f9baf4d5b1d6acdbc5
Source dataset
uspto-grants-1996_09
Patent number
US05552551

Reaction notes

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