2-Fluoroanisole → 1-(3-Fluoro-4-methoxy-phenyl)-5-methyl-hexan-1-one

HRID 1683445Notes

Reaction equation

HRID 1683445 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][CH:6]([CH3:13])[CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22]>[N+](C1C=CC=CC=1)([O-])=O>[F:14][C:15]1[CH:20]=[C:19]([C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH:6]([CH3:13])[CH3:5])[CH:18]=[CH:17][C:16]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 675762-FluoroanisoleHCID 6451240Aluminum(III) ChlorideHCID 136648655-Methylhexanoyl chloride

Product 1

HCID 190437661-(3-Fluoro-4-methoxy-phenyl)-5-methyl-hexan-1-one

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

14 ml of nitrobenzene are cooled in an ice-bath and then mixed in succession with 3.8 g of AlCl3 and 3.7 g of 5-methyl-hexanoyl chloride in 5 ml of nitrobenzene. The mixture is stirred and then treated with 2.7 ml of 2-fluoro-anisole. The solution is stirred overnight, then poured into ice-water and extracted with methylene chloride. The extracts are washed with water and 10% aqueous NaCl solution, and thereafter dried and concentrated and recrystallized using pentane. 5.31 g of 1-(3-fluoro-4-methoxy-phenyl)-5-methyl-hexan-1-one, MS: m/e 238 (M+), are obtained.

Workup

  1. stirringThe solution is stirred overnight
  2. extractionextracted with methylene chloride
  3. washThe extracts are washed with water and 10% aqueous NaCl solution
  4. customdried
  5. concentrationconcentrated
  6. customrecrystallized

Sources & evidence

ORD record
ord-840649291d574753b3dfca7faf1eb9bc
Source dataset
uspto-grants-1997_06
Patent number
US05637771

Reaction notes

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