Ethanol → ethyl 2,3-dihydro-1H-indene-2-carboxylate

HRID 978765Notes

Reaction equation

HRID 978765 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1([C:13]([OH:15])=[O:14])C(O)=O.S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[C:13]([O:15][CH2:21][CH3:22])=[O:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2519571,3-Dihydroindene-2,2-dicarboxylic acid

Product 1

HCID 15280733ethyl 2,3-dihydro-1H-indene-2-carboxylate

Procedure

11.7 g of 2,2-indandicarboxylic acid was heated at 200° C. for 30 minutes. After liberation of bubbles ceased, the reaction product was cooled and dissolved in 150 ml of ethanol. 4 ml of concentrated sulfuric acid was added to the solution and the mixture was heated under reflux for 4 hours. The reaction mixture was concentrated in vacuo and the residue was neutralized by addition of sodium carbonate. The mixture was extracted with chloroform. The extract was washed with water and dried and then concentrated in vacuo to give 9.4 g of ethyl 2-indancarboxylate as an oil.

Workup

  1. temperaturethe reaction product was cooled
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 4 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additionthe residue was neutralized by addition of sodium carbonate
  6. extractionThe mixture was extracted with chloroform
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-adfbc1752cb74f4b9ef20c01413cd620
Source dataset
uspto-grants-1987_05
Patent number
US04665188

Reaction notes

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