4-Nitrobenzaldehyde → HCID 22916912, compound

HRID 1376832Notes

Reaction equation

HRID 1376832 reaction equation
Cl[CH:2]([Cl:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)([O-:13])=[O:12].O>O1CCCC1>[Cl:10][C:2]1([C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[CH:18]([C:17]2[CH:16]=[CH:15][C:14]([N+:11]([O-:13])=[O:12])=[CH:21][CH:20]=2)[O:19]1

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 962WaterHCID 30164831,1-Dimethylethyl dichloroacetate

Product 1

HCID 22916912HCID 22916912, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

5.55 g of tert.-butyl dichloroacetate in 30 ml of tetrahydrofuran and 4.99 g of 4-nitrobenzaldehyde in 30 ml of tetrahydrofuran were cooled to -20° C. and, over 20 minutes, 30 ml of a molar solution of potassium tert.-butylate in tetrahydrofuran were added dropwise at -20° C. The reaction mixture was stirred while the temperature was allowed to rise to 20° C., and it was then poured into 100 ml of water and ice, and was extracted with ether. The organic phase was washed with water saturated with sodium chloride, then with water, dried, and concentrated to dryness under reduced pressure. The residue was chromatographed on silica and eluted with methylene chloride to obtain 6.44 g of 1,1-dimethylethyl 2-chloro-3-(4-nitrophenyl)oxirane carboxylate melting at 60° C.

Workup

  1. customto rise to 20° C.
  2. extractionwas extracted with ether
  3. washThe organic phase was washed with water saturated with sodium chloride
  4. dry with materialwith water, dried
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was chromatographed on silica
  7. washeluted with methylene chloride

Sources & evidence

ORD record
ord-60fadf5be787429aab729c8f5afc0d3d
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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