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

HRID 848511Notes

Reaction equation

HRID 848511 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-b523152ade4e47c5a03f19c7517aab86
Source dataset
uspto-grants-1981_10
Patent number
US04296122

Reaction notes

Loading…