Acetyl chloride → HCID 20447343, compound

HRID 2417629Notes

Reaction equation

HRID 2417629 reaction equation
FC1C=[C:4](C=CC=1)[CH:5]=[O:6].[N+]([CH:13]([OH:15])[CH3:14])([O-])=O.C(OC(=O)C)(=O)C.[F:23][C:24]1[CH:25]=[C:26]([CH:30]([OH:37])[CH:31]([N+:34]([O-:36])=[O:35])[CH2:32][OH:33])[CH:27]=[CH:28][CH:29]=1.C(Cl)(=O)C>C(N(CC)CC)C>[F:23][C:24]1[CH:25]=[C:26]([CH:30]([O:37][C:5](=[O:6])[CH3:4])[CH:31]([N+:34]([O-:36])=[O:35])[CH2:32][O:33][C:13](=[O:15])[CH3:14])[CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 5

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 680093-FluorobenzaldehydeHCID 20447360HCID 20447360, compoundHCID 22056827Nitroethanol

Product 1

HCID 20447343HCID 20447343, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

0.5 ml of triethylamine catalyst are added to a mixture of 6.0 g (0.05 moles) of 3-fluorobenzaldehyde and 4.5 g (0.05 moles) of nitroethanol. The mixture is stirred for one hour and then allowed to stand at 0° C. for 72 hours. 15 g (0.15 moles) of acetic anhydride are added under stirring to the resulting crude 1-(3-fluorophenyl)-2-nitro-1,3-propanediol, and then 2 ml of acetyl chloride are added dropwise to the mixture. The mixture is stirred at 50° C. for 2 hours and then poured onto 100 g of ice under stirring. The resulting oily product starts to crystallize within about 15 minutes. The crude product is separated from the water, dissolved in 50 ml of chloroform, the solution is washed acid-free with ice-cold water, decolourized with activated carbon, filtered, and the solvent is evaporated under reduced pressure. 10.8 g (72%) of the title compound are obtained; m.p.: 94° C.

Workup

  1. waitto stand at 0° C. for 72 hours
  2. stirringThe mixture is stirred at 50° C. for 2 hours
  3. stirringunder stirring
  4. customto crystallize within about 15 minutes
  5. customThe crude product is separated from the water
  6. dissolutiondissolved in 50 ml of chloroform
  7. washthe solution is washed acid-free with ice-cold water
  8. filtrationfiltered
  9. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-ab8a6b5340d84826b032677781c1b0b4
Source dataset
uspto-grants-1984_09
Patent number
US04469703

Reaction notes

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