4-Hydroxybenzaldehyde → HCID 2781383, compound

HRID 486292Notes

Reaction equation

HRID 486292 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[ClH:20]>C(O)C>[Cl:20][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH:2]=[CH:16][C:15]1[CH:18]=[CH:19][C:12]([OH:11])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 107572-Chloroacetophenone

Product 1

HCID 2781383HCID 2781383, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 g of 2-chloro acetophenone and 15.8 g 4-hydroxy benzaldehyde were dissolved in 100 ml ethanol saturated with gaseous hydrochloric acid and the mixture was left at ambient temperature for 3 days. The ethanol was concentrated in vacuo. The residue was dissolved in 200 ml isopropanol, after which 500 ml water was added with agitation and the precipitate was filtered. The yield after recrystallization from isopropanol was 25.4 g of the expected chalcone.

Workup

  1. concentrationThe ethanol was concentrated in vacuo
  2. dissolutionThe residue was dissolved in 200 ml isopropanol
  3. additionafter which 500 ml water was added with agitation
  4. filtrationthe precipitate was filtered
  5. customThe yield
  6. customafter recrystallization from isopropanol

Sources & evidence

ORD record
ord-d5171e9bcd694c09a8b9e3a8e0de37c2
Source dataset
uspto-grants-1994_03
Patent number
US05290951

Reaction notes

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