Hydrochloric Acid → Ethyl 6-acetyl-1,4-benzodioxin-2-carboxylate

HRID 1756024Notes

Reaction equation

HRID 1756024 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[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].Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10987416Ethyl 1,4-benzodioxin-2-carboxylate

Product 1

HCID 11806994Ethyl 6-acetyl-1,4-benzodioxin-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Slowly add 8.1 g (60.7 mmol) of aluminium chloride to a solution of 2.85 g (36.3 mmol) of acetyl chloride and 5 g (24.7 mmol) of ethyl 1,4-benzodioxin-2-carboxylate in 120 cm3 of carbon disulfide at 0° C. Stir for 4 hours at room temperature and then, after acid hydrolysis with 20 cm3 of 2N hydrochloric acid, extract the reaction mixture with methylene chloride. After drying the methylene chloride phase over magnesium sulfate, concentrating to dryness and washing with ethanol, ethyl 6-acetyl-1,4-benzodioxin-2-carboxylate is obtained in a yield of 95%. Melting point: 122° C. ##STR30##

Workup

  1. customat 0° C
  2. extractionextract the reaction mixture with methylene chloride
  3. dry with materialAfter drying the methylene chloride phase over magnesium sulfate
  4. concentrationconcentrating to dryness
  5. washwashing with ethanol

Sources & evidence

ORD record
ord-52e3717d16c747f6a751bb4c2d3ae354
Source dataset
uspto-grants-1995_08
Patent number
US05439909

Reaction notes

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