Hydrochloric Acid → 1-(3-Fluoro-4-methoxyphenyl)hexan-1-one

HRID 7887

Reaction equation

HRID 7887 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13].[C:14](Cl)(=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].Cl>>[F:5][C:6]1[CH:11]=[C:10]([C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:9]=[CH:8][C:7]=1[O:12][CH3:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 67340Hexanoyl chlorideHCID 675762-FluoroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 219909101-(3-Fluoro-4-methoxyphenyl)hexan-1-oneYield 90.4%

Procedure

Aluminum chloride (6.5 g, 48.8 mmol) was added to a stirred mixture of 1-fluoro-2-methoxybenzene (5.0 mL, 44.4 mmol) and hexanoyl chloride (7.5 mL, 53.3 mmol) at room temperature. The mixture warmed and HCl evolution occurred. The resulting mixture was stirred at room temperature for 45 minutes and then partitioned between EtOAc (100 mL) and water (100 mL). The EtOAc layer was washed with water (100 mL), aqueous K2CO3 (100 mL) and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to yield crude 1-(3-fluoro-4-methoxyphenyl)-1-hexanone (9 g) as a solid.

Workup

  1. temperatureThe mixture warmed
  2. custompartitioned between EtOAc (100 mL) and water (100 mL)
  3. washThe EtOAc layer was washed with water (100 mL), aqueous K2CO3 (100 mL) and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-964e1b3c9e4a4ee4925791c3c6f268ce
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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