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

HRID 2397050Notes

Reaction equation

HRID 2397050 reaction equation
[CH3:1][CH:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18]>[N+](C1C=CC=CC=1)([O-])=O>[F:10][C:11]1[CH:16]=[C:15]([C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH:2]([CH3:9])[CH3:1])[CH:14]=[CH:13][C:12]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 675762-FluoroanisoleHCID 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 AICl3 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-1d88f9f47f344edab8d38287517f9503
Source dataset
uspto-grants-1996_02
Patent number
US05495048

Reaction notes

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