Water → 4-Fluorochalcone

HRID 232113Notes

Reaction equation

HRID 232113 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].O.[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1>C(O)C>[F:13][C:14]1[CH:21]=[CH:20][C:17](/[CH:18]=[CH:2]/[C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 53669884-Fluorochalcone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

52.0 g. (433 mmoles) of acetophenone is added to a solution of 21.8 g. (545 mmoles) of sodium hydroxide in a mixture of 196 ml. of water and 122.5 ml. of 95% ethanol stirred at 20°-25° C., the resulting suspension is cooled to 0°-5° C., and 53.74 g. (433 mmoles) of 4-fluorobenzaldehyde is added portionwise, the temperature of the reaction mixture rising to 20° C. during the addition. The solidified reaction mixture is kept at 20°-25° C. for 3 hours and refrigerated for 16 hours. The solid is collected by filtration, rinsed with about 2 l. of water until the rinses are neutral, rinsed with 200 ml. of cold 95% ethanol and recrystallized from 95% ethanol to obtain the product as yellow flakes (66.25 g. (68%)), m.p. 83°-86° C.

Workup

  1. temperaturethe resulting suspension is cooled to 0°-5° C.
  2. additionthe temperature of the reaction mixture rising to 20° C. during the addition
  3. customThe solidified reaction mixture
  4. waitrefrigerated for 16 hours
  5. filtrationThe solid is collected by filtration
  6. washrinsed with about 2 l
  7. washrinsed with 200 ml
  8. customof cold 95% ethanol and recrystallized from 95% ethanol
  9. customto obtain the product as yellow flakes (66.25 g. (68%)), m.p. 83°-86° C.

Sources & evidence

ORD record
ord-c62947ac272b45399ab0e163b9542d93
Source dataset
uspto-grants-1989_07
Patent number
US04851427

Reaction notes

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