Ethyl Acetate → HCID 22115898, compound

HRID 1598988Notes

Reaction equation

HRID 1598988 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11].[CH3:13][O:14][C:15]1[C:16](OC)=[C:17]([O:21][CH3:22])[CH:18]=[CH:19][CH:20]=1.[C:25](OCC)(=[O:27])C>ClCCCl>[Cl:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([C:16]1[C:17]([O:21][CH3:22])=[CH:18][C:19]([O:27][CH3:25])=[CH:20][C:15]=1[O:14][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 124621,2,3-TrimethoxybenzeneHCID 740895-Chlorovaleryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22115898HCID 22115898, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

The following is the preparation of a compound of Formula 3 in which A mixture of aluminum chloride (22.6 g, 170 mmol), 5-chlorovaleryl chloride (26.4 g, 170 mmol), and 1,2-dichloroethane (200 mL) was stirred for 30 minutes, and then filtered. The filtrate was added to a solution of trimethoxybenzene (26.7 g, 158 mmol) in 1,2-dichloroethane (100 mL); with reaction mixture warming spontaneously to approximately 50° C. Thin layer chromatography of a water-quenched sample taken after four hours showed complete reaction. The reaction mixture was poured over ice, and ethyl acetate was added to extract the product. The ethyl acetate phase was washed twice with water and once with brine, then dried over anhydrous sodium sulfate. The solution was filtered and the solvent removed, then the resulting oil was dissolved in a warm 20% solution of ethyl acetate in hexane (250 mL). The solution was allowed to crystallize at room temperature for five hours, then at 4° C. for one hour. Filtration, washing the crystals with 10% ethyl acetate in hexane, and air-drying afforded 5-chloro-1-(2,4,6-trimethoxyphenyl)-1-pentanone, 34 g (83% yield), m.p. 53°-55° C.

Workup

  1. filtrationfiltered
  2. customwith reaction mixture
  3. customThin layer chromatography of a water-quenched sample
  4. waittaken after four hours
  5. customreaction
  6. additionwas added
  7. extractionto extract the product
  8. washThe ethyl acetate phase was washed twice with water and once with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationThe solution was filtered
  11. customthe solvent removed
  12. dissolutionthe resulting oil was dissolved in a warm 20% solution of ethyl acetate in hexane (250 mL)
  13. customto crystallize at room temperature for five hours
  14. waitat 4° C. for one hour
  15. filtrationFiltration
  16. washwashing the crystals with 10% ethyl acetate in hexane
  17. customair-drying

Sources & evidence

ORD record
ord-5c35be59a7f24b0998e2912b57f6f27a
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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