Acetyl chloride → Ethyl 6-acetyl-1,4-benzodioxin-2-carboxylate

HRID 2393512Notes

Reaction equation

HRID 2393512 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:7])[CH3:6].[O:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH:11]=[C:10]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(=S)=S>[C:5]([C:17]1[CH:16]=[CH:15][C:14]2[O:9][C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][O:12][C:13]=2[CH:18]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10987416Ethyl 1,4-benzodioxin-2-carboxylate

Product 1

HCID 11806994Ethyl 6-acetyl-1,4-benzodioxin-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

12.5 g of aluminum trichloride are added to a mixture of 4.27 g of acetyl chloride and 7.5 g of ethyl 1,4-benzodioxin-2-carboxylate in 150 ml of carbon disulfide at 0° C. The reaction mixture is stirred at room temperature for 14 hours. After acid hydrolysis with 50 ml of hydrochloric acid (2N) and extraction of the aqueous phase with dichloromethane, the organic phase is washed with saturated sodium hydrogen carbonate solution and then dried over magnesium sulfate. The acylated product is purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate, 7:3).

Workup

  1. customAfter acid hydrolysis
  2. extractionwith 50 ml of hydrochloric acid (2N) and extraction of the aqueous phase with dichloromethane
  3. washthe organic phase is washed with saturated sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe acylated product is purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-9301f14740614bc08d4370d2bbf5d2bb
Source dataset
uspto-grants-1998_09
Patent number
US05807882

Reaction notes

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