Ethanol → HCID 20310097, compound

HRID 1763447Notes

Reaction equation

HRID 1763447 reaction equation
S(=O)(=O)(O)O.[C:6]([C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][CH2:17][CH:18]2[C:23]([OH:25])=[O:24])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:26](O)[CH3:27]>>[C:6]([C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][CH2:17][CH:18]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1621494-Benzoyl-2,3-dihydro-1H-indene-1-carboxylic acid

Product 1

HCID 20310097HCID 20310097, compound

Procedure

To 250 ml. of ethanol is added 20 ml. of concentrated sulfuric acid, followed by the addition of 13.3 g. of 4-benzoylindan-1-carboxylic acid. The mixture is refluxed for 5.5 hours. After cooling, the ethanol is distilled off under reduced pressure and water is added to the residue, followed by extraction with ether. The ethereal layer is washed with a 5% aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride and, then, dried. The solvent is distilled off under reduced pressure and the residue is purified by column chromatography on silica gel (eluted with chloroform). The described procedure gives ethyl 4-benzoylindan-1-carboxylate as an oily product. Infrared absorption spectrum (neat)

Workup

  1. temperatureThe mixture is refluxed for 5.5 hours
  2. temperatureAfter cooling
  3. distillationthe ethanol is distilled off under reduced pressure and water
  4. additionis added to the residue
  5. extractionfollowed by extraction with ether
  6. washThe ethereal layer is washed with a 5% aqueous solution of sodium hydroxide
  7. dry with materiala saturated aqueous solution of sodium chloride and, then, dried
  8. distillationThe solvent is distilled off under reduced pressure
  9. customthe residue is purified by column chromatography on silica gel (eluted with chloroform)

Sources & evidence

ORD record
ord-4efa8bca091c4a988b8127e0bd014959
Source dataset
uspto-grants-1978_09
Patent number
US04111997

Reaction notes

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