Hydrochloric Acid → HCID 14461243, compound

HRID 1708863Notes

Reaction equation

HRID 1708863 reaction equation
[Mg].[F:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.Cl>CCOCC>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]([OH:17])[CH2:7][C:6]2[CH:9]=[CH:10][C:3]([F:2])=[CH:4][CH:5]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 96024-Fluorobenzyl chlorideHCID 680234-FluorobenzaldehydeHCID 5462224Magnesium

Product 1

HCID 14461243HCID 14461243, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

Under a nitrogen atmosphere, 2.04 g (0.08 mol) of magnesium are covered with ether. 12.2 g (0.08 mol) of 4-fluorobenzyl chloride in 20 ml of ether are added dropwise to this in such a way that the ether boils gently. After addition is complete, the mixture is refluxed for a further 30 minutes, cooled to room temperature, and 8.3 g (0.07 mol) of 4-fluorobenzaldehyde in 20 ml of ether are slowly added dropwise. It may be necessary to cool with ice-water if the solution boils. After addition is complete, the mixture is left to reflux for 2 hours, then cooled and poured into 50 ml of ice-water. 50% concentrated hydrochloric acid is used to acidify, the phases are separated, and the aqueous phase is extracted 5 x with ether. The combined org. phases are neutralized with saturated sodium bicarbonate solution, washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated. The colorless oil crystallizes completely and yields 15.7 g of white crystals.

Workup

  1. additionAfter addition
  2. temperaturethe mixture is refluxed for a further 30 minutes
  3. additionAfter addition
  4. waitthe mixture is left
  5. temperatureto reflux for 2 hours
  6. temperaturecooled
  7. customthe phases are separated
  8. extractionthe aqueous phase is extracted 5 x with ether
  9. washwashed with saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. customevaporated
  12. customThe colorless oil crystallizes completely

Sources & evidence

ORD record
ord-9d72150de681449ea5e09dcc10ed4c80
Source dataset
uspto-grants-1990_08
Patent number
US04946841

Reaction notes

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