Hydrochloric Acid → HCID 67767564, compound

HRID 742082Notes

Reaction equation

HRID 742082 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][C:13]([CH:16]=[O:17])=[CH:12]1.[OH-:18].[Na+].Cl>C(O)C.O>[OH:18][C:13]1([C:16]2[O:17][C:6]3[C:5]([C:3](=[O:4])[CH:2]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:14]=[CH:15][S:11][CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 681353-ThiophenecarboxaldehydeHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 67767564HCID 67767564, compoundYield 36%

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 thiophene 3-carboxaldehyde 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: 36%. Quantum Yield: (1.8 relative to 3HF in methyl cyclohexane), Extinction coefficient: εmax (M-1 cm-1)=2000. λmax (abs)=343 nm and λmax (em)=526 nm. MP=195°-196° C.

Sources & evidence

ORD record
ord-91eb1a7be0124601938f78a5647a1cf1
Source dataset
uspto-grants-1996_09
Patent number
US05552551

Reaction notes

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