1-Fluoronaphthalene → Ethyl 6-(4-fluoro-1-naphthyl)-6-oxohexanoate

HRID 747456

Reaction equation

HRID 747456 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Cl-].[CH2:13]([O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:24])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 94501-FluoronaphthaleneHCID 6451240Aluminum(III) ChlorideHCID 86624202Adipic acid monoethyl ester chloride

Product 1

HCID 18174724Ethyl 6-(4-fluoro-1-naphthyl)-6-oxohexanoateYield 69.8%

Procedure

To a mixture of 1-fluoronaphthalene (20.0 g) and adipic acid monoethyl ester chloride (27.5 g) was added gradually aluminum chloride (38.5 g) with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water (500 ml) and extracted with diethyl ether (200 ml×2). The organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (200 ml), dried over anhydrous magnesium sulfate, and concentrated to give ethyl 6-(4-fluoro-1-naphthyl)-6-oxohexanoate as an oil (27.7 g, 67%).

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 2 hours
  3. extractionextracted with diethyl ether (200 ml×2)
  4. washThe organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (200 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3925506ddffd4f8e92c65f7cb569b870
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Linked notes

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