Ethylene → HCID 89464145, compound

HRID 2167114Notes

Reaction equation

HRID 2167114 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:19][C:20]([OH:22])=O)[CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16].[Cl-].[Al+3].[Cl-].[Cl-].C=C.[S:29](=[O:32])([OH:31])[O-:30].[Na+]>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C.O>[OH:22][C:20]1([S:29]([OH:32])(=[O:31])=[O:30])[CH2:2][CH2:1][C:12]2[C:11](=[CH:10][C:9]([O:8][CH3:7])=[C:14]([O:15][CH3:16])[C:13]=2[O:17][CH3:18])[CH2:19]1

Participants

10

Reactant 5

HCID 6325EthyleneHCID 65578Oxalyl chlorideHCID 703723,4,5-Trimethoxyphenylacetic acidHCID 6451240Aluminum(III) ChlorideHCID 23665763Sodium Bisulfite

Product 1

HCID 89464145HCID 89464145, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

Oxalyl chloride (14.7 g) was added over 10 minutes to a solution of 3,4,5-trimethoxyphenylacetic acid (23.8 g) in DCM (400 ml) and DMF (5 drops). The mixture was stirred at ambient temperature for 18 hours. The solvents were removed under vacuum to give an orange oil which was redissolved in DCM (100 ml) and then added to a solution of aluminium chloride (43.3 g) in DCM (1.0 L) at 5° C. The mixture was stirred at 5° C. for 10 minutes before ethylene gas was gently bubbled through the mixture for 1 hour. The crude reaction mixture was poured on to ice/water and stirred vigorously for 20 minutes. The organic phase was separated and washed with a aqueous 2N HCl solution, saturated aqueous NaHCO3 solution and brine, dried (MgSO4) and filtered. The solvents were removed under vacuum to give a dark oil that was redissolved in ethyl acetate (60 ml). Sodium bisulfite (28.6 g) in water (60 ml) was added to the mixture, stirring for 18 hours. A precipitate was removed by filtration, washed with ethyl acetate and dried under vacuum.

Workup

  1. customThe solvents were removed under vacuum
  2. customto give an orange oil which
  3. customwas gently bubbled through the mixture for 1 hour
  4. customThe crude reaction mixture
  5. stirringstirred vigorously for 20 minutes
  6. customThe organic phase was separated
  7. washwashed with a aqueous 2N HCl solution, saturated aqueous NaHCO3 solution and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe solvents were removed under vacuum
  11. customto give a dark oil that
  12. stirringstirring for 18 hours
  13. customA precipitate was removed by filtration
  14. washwashed with ethyl acetate
  15. customdried under vacuum

Sources & evidence

ORD record
ord-5d2ef21b8bb74145a4adac38808427dc
Source dataset
uspto-grants-2015_06
Patent number
US09044463B2

Reaction notes

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