Acetone → HCID 21547110, compound

HRID 1605643Notes

Reaction equation

HRID 1605643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1.[CH3:16][C:17]([CH3:19])=[O:18].CO.[OH-].[K+]>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11](/[CH:14]=[CH:16]/[C:17](=[O:18])[CH3:19])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 14797Potassium HydroxideHCID 13928932'-Fluorobiphenyl-4-carbaldehyde

Product 1

HCID 21547110HCID 21547110, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200.2 Gm (1.0 mol) of 2'-fluoro-4-biphenyl-carboxaldehyde, 3500 gm (60.3 mols) of acetone and 200 ml of methanol were charged into a 6-liter three-neck-flask equipped with a stirrer, a dropping funnel and an internal thermometer. While thoroughly stirring the contents of the flask, a solution of 2.805 gm (0.05 mol) of potassium hydroxide in 16 ml of water was added dropwise thereto while maintaining a reaction temperature of 20° to 25°C, and the resulting mixture was stirred for three hours more. Thereafter, the precipitated solid side product was filtered off, the filtrate was made neutral by dropwise addition of glacial acetic acid, and the neutral solution was evaporated in vacuo. The residue was recrystallized three times from diisopropyl ether and then once from a mixture of ethyl acetate and diisopropyl ether (volumetric ratio 1:1) in the presence of activated charcoal, yielding 101.2 gm (42% of theory) of the fallow crystalline compound of the formula ##SPC20##

Workup

  1. customequipped with a stirrer, a dropping funnel
  2. temperaturewhile maintaining a reaction temperature of 20° to 25°C
  3. stirringthe resulting mixture was stirred for three hours more
  4. filtrationThereafter, the precipitated solid side product was filtered off
  5. additionthe filtrate was made neutral by dropwise addition of glacial acetic acid
  6. customthe neutral solution was evaporated in vacuo
  7. customThe residue was recrystallized three times from diisopropyl ether
  8. additiononce from a mixture of ethyl acetate and diisopropyl ether (volumetric ratio 1:1) in the presence of activated charcoal
  9. customyielding 101.2 gm (42% of theory) of the fallow crystalline compound of the formula

Sources & evidence

ORD record
ord-6e31921b34ef4237a5813025287d4571
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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