Hydrochloric Acid → HCID 67767312, compound

HRID 742081Notes

Reaction equation

HRID 742081 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=[O:17].[OH-:18].[Na+].Cl>C(O)C.O>[OH:18][C:13]1[CH:14]=[CH:15][S:11][C:12]=1[C:16]1[O:17][C:6]2[C:5]([C:3](=[O:4])[CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73642-ThiophenecarboxaldehydeHCID 14798Sodium HydroxideHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 67767312HCID 67767312, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3 g (22.2 mmol) of 2-hydroxyacetophenone, 2.5 g (22.2 mmol) of 2-thiophenecarboxaldehyde and 3 g NaOH (in 15 ml of water) in 50 ml of ethanol was stirred for 12 hours before the solution was poured into 300 ml of water. The resulting mixture was neutralized with dilute HCl to yield a chalcone. The yellow precipitate obtained was filtered and dried. The product 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 300 ml water and acidified with dilute HCl. Yellow precipitate obtained was filtered and dried. Product was recrystallized from THF/hexane mixture. Yield: 46%. Quantum Yield: (1.25 relative to 3HF in methyl cyclohexane), Extinction Coefficient: εmax (M-1 cm-1)=22000. λmax (abs)=355 nm and λmax (em)=545 nm. MP=202°-203° C.

Sources & evidence

ORD record
ord-1af08a5eeee04deca330a13d31d0de29
Source dataset
uspto-grants-1996_09
Patent number
US05552551

Reaction notes

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