Pentanal → HCID 53793731, compound

HRID 2292407Notes

Reaction equation

HRID 2292407 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[CH:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18].[Cl-].[NH4+]>C1COCC1>[F:6][C:7]1[C:8]([F:13])=[CH:9][CH:10]=[CH:11][C:12]=1[CH:14]([OH:19])[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 8063PentanalHCID 97061,2-DifluorobenzeneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 53793731HCID 53793731, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (50 cm3, 10.0M in hexanes, 0.5 mol) was added dropwise to a stirred, cooled (-78° C.) solution of 1,2-difluorobenzene (57 g, 0.5 mol) in dry THF (600 cm3) under an atmosphere of dry nitrogen. The mixture was maintained under these conditions (3 h) then a solution of pentanal (43.1 g, 0.5 mol), in dry THF (50 cm3) added dropwise at -78° C. The temperature of the reaction mixture was allowed to reach room temperature overnight. An aqueous solution of ammonium chloride (27 g in 160 cm3 water) was added and the product extracted into diethyl ether (2×150 cm3), the combined extracts washed with water (2×150 cm3) and dried (MgSO4). The solvent was removed in vacuo to give the product as a colourless oil which was purified by distillation under reduced pressure.

Workup

  1. temperatureThe mixture was maintained under these conditions (3 h)
  2. extractionthe product extracted into diethyl ether (2×150 cm3)
  3. washthe combined extracts washed with water (2×150 cm3)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d95c4d86c4e443c1b8ec64c96284b8f6
Source dataset
uspto-grants-1997_11
Patent number
US05683623

Reaction notes

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