Aluminum(III) Chloride → HCID 601767, compound

HRID 2106050Notes

Reaction equation

HRID 2106050 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[F:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:18])[CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:8][CH:7]=1>C(=S)=S>[F:5][C:6]1[CH:7]=[C:8]2[C:9](=[CH:10][CH:11]=1)[O:12][C:13](=[O:18])[CH2:14][C:15]2([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 19181162HCID 19181162, compound

Product 1

HCID 601767HCID 601767, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a stirred suspension of aluminum trichloride (18.0 g) in carbon disulfide (30 mL) was added dimethylacrylate 4-fluorophenyl ester (18.0 g, 92.7 mmol) dropwise over a 0.5 hour period. The reaction mixture was stirred at room temperature for 14.0 hours. The reaction was poured onto ice and extracted with ethyl acetate-hexanes (1:10, 200 mL). The organic phase was washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and evaporated in vacuo. Trituration of the residue with cold hexane gave a colorless crystalline 6-fluoro-4,4-dimethylchroman-2-one (13.9 g, 77%).

Workup

  1. additionThe reaction was poured onto ice
  2. extractionextracted with ethyl acetate-hexanes (1:10, 200 mL)
  3. washThe organic phase was washed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-af359770d1f54836b50311d6f585553a
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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