Hydrochloric Acid → HCID 20310097, compound

HRID 1606735Notes

Reaction equation

HRID 1606735 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C(=S)=S>[C:19]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH2:7][CH2:6][CH:5]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12397744HCID 12397744, compound

Product 1

HCID 20310097HCID 20310097, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent3×

Procedure

To 120 ml. of carbon disulfide is added 54 g. of anhydrous aluminum chloride powder on an ice bath, followed by the dropwise addition of a solution of 11.4 g. of ethyl indan-1-carboxylate in 60 ml. of carbon disulfide. The mixture is stirred for 10 minutes, after which a solution of 42 g. of benzoyl chloride in 60 ml. of carbon disulfide is added dropwise. After the dropwise addition has been completed, the temperature is gradually increased and the solution is stirred on reflux for 3 hours and thirty minutes to complete the reaction. Ice and hydrochloric acid are added to the reaction mixture followed by extraction with ether. The extract is washed with 1N hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in the order mentioned and, then, dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is column-chromatographed on silica gel (conditions: 2 Kg. of silica gel; eluant solvent-benzene containing 2.5 % of ethyl acetate). The first-emerging fractions rich in ethyl 4-benzoylindan-1-carboxylate are pooled separate from the ensuing fractions rich in ethyl 6-benzoylindan-1-carboxylate. The former fractions are further purified by rechromatography on a column of silica gel, whereby ethyl 4-benzoylindan-1-carboxylate is obtained as an oily product.

Workup

  1. additionAfter the dropwise addition
  2. temperaturethe temperature is gradually increased
  3. stirringthe solution is stirred
  4. temperatureon reflux for 3 hours and thirty minutes
  5. customthe reaction
  6. extractionfollowed by extraction with ether
  7. washThe extract is washed with 1N hydrochloric acid, water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent is then distilled off under reduced pressure
  10. customthe residue is column-chromatographed on silica gel (conditions: 2 Kg. of silica gel; eluant solvent-benzene containing 2.5 % of ethyl acetate)
  11. customThe first-emerging fractions rich in ethyl 4-benzoylindan-1-carboxylate are pooled separate from the ensuing fractions rich in ethyl 6-benzoylindan-1-carboxylate
  12. customThe former fractions are further purified by rechromatography on a column of silica gel

Sources & evidence

ORD record
ord-0e314bfa74ea4e4e92bfac5e7ea652c8
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

Loading…