Ethanol → Ethyl 6,7-dichloro-2,3-dihydro-1-benzofuran-2-carboxylate

HRID 261030Notes

Reaction equation

HRID 261030 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:14].S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[CH2:20]([O:10][C:9]([CH:7]1[CH2:6][C:5]2[CH:12]=[CH:13][C:2]([Cl:1])=[C:3]([Cl:14])[C:4]=2[O:8]1)=[O:11])[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 98160656,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic Acid

Product 1

HCID 12747889Ethyl 6,7-dichloro-2,3-dihydro-1-benzofuran-2-carboxylate

Procedure

A solution of 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid (70 g.) conc. sulfuric acid (2 ml.) and ethanol (250 ml.) is refluxed for 2 hours. The ethanol is distilled at reduced pressure and the residue is suspended in saturated sodium bicarbonate and extracted with ether. The ether solution is washed with brine, dried over magnesium sulfate and the ether distilled at reduced pressure. The 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid ethyl ester is used without further purification in the following synthesis.

Workup

  1. distillationThe ethanol is distilled at reduced pressure
  2. extractionextracted with ether
  3. washThe ether solution is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. distillationthe ether distilled at reduced pressure
  6. customThe 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid ethyl ester is used without further purification in the following synthesis

Sources & evidence

ORD record
ord-1718803079f446fa983fdea10cd38125
Source dataset
uspto-grants-1979_08
Patent number
US04163794

Reaction notes

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