4-Hydroxybenzaldehyde → HCID 134561, compound

HRID 921479Notes

Reaction equation

HRID 921479 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH3:18])=[CH:13][CH:12]=1.C(OCC)C.S(=O)(=O)(O)O>C(O)C>[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:6]([C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=2)=[O:7])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 74694'-Hydroxyacetophenone

Product 1

HCID 134561HCID 134561, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 4-hydroxybenzaldehyde (0.488 g, 4 mmole) and 4′-hyroxyacetophenone (0.66 g, 4.84 mmole) are introduced to a 25 mL flask and dissolved completely by adding 10 mL of diethyl ether and 4 mL of ethanol thereto. Next, 4 mL of sulfuric acid is introduced thereto and the reaction mixture is agitated for 3 hours. The reaction mixture is precipitated in water (300 mL) and filtered to obtain a solid, which in turn is washed with distilled water three times, dried under vacuum, and purified by column chromatography using diethyl ether/hexane (1/1, v/v) as eluent to obtain 4,4′-dihydroxychalcone (DHC) having the following structure. The resultant product has a yield and melting point of 30% and 203° C., respectively.

Workup

  1. dissolutiondissolved completely
  2. customThe reaction mixture is precipitated in water (300 mL)
  3. filtrationfiltered
  4. customto obtain a solid, which in turn
  5. washis washed with distilled water three times
  6. customdried under vacuum
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-b1b1a831cd494f869186749514ffc95b
Source dataset
uspto-grants-2016_03
Patent number
US09273181B2

Reaction notes

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