Hydrochloric Acid → 4,7-Dimethyl-1-indanone

HRID 1937029Notes

Reaction equation

HRID 1937029 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1.[C:13](Cl)(=[O:16])[CH:14]=[CH2:15].Cl>C(Cl)Cl.O>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:7]=1[CH2:15][CH2:14][C:13]2=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7809P-XyleneHCID 13140Acryloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2200944,7-Dimethyl-1-indanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

180 mL CH2Cl2 and 36 g anhydrous AlCl3 (Carlo Erba) were charged in a 3-neck 0.5-L round bottomed flask equipped with magnetic stirring bar, 250-ml dropping funnel, thermometer and reflux condenser. A solution containing 31 ml p-xylene and 21 ml acryloylchloride (Aldrich) in 100 ml CH2Cl2 was placed in the dropping funnel. This solution was added dropwise over 4 hours to the flask, the content of which was kept under stirring at the temperature of 0° C. with a bath of water and ice. Evolution of HCl was observed and the reaction mixture turned dark brick-red. After addition was complete, the mixture was allowed to warm to room temperature and stirring was continued overnight (18 hours). The reaction mixture was poured in a flask containing 250 g ice and 250 ml HCl 37%, the organic phase was separated and the acqueous phase was extracted with Et2O (3 times). All organic fractions were combined and washed with saturated aqueous NaHCO3 and water, dried with Na2SO4, filtered and the solvent was removed in vacuo. 38.25 g of light yellow-orange oil were obtained. This product was used without any further purification.

Workup

  1. customequipped with magnetic stirring bar
  2. temperaturethermometer and reflux condenser
  3. additionThis solution was added dropwise over 4 hours to the flask
  4. additionAfter addition
  5. custom(18 hours)
  6. additionThe reaction mixture was poured in a flask
  7. customthe organic phase was separated
  8. extractionthe acqueous phase was extracted with Et2O (3 times)
  9. washwashed with saturated aqueous NaHCO3 and water
  10. dry with materialdried with Na2SO4
  11. filtrationfiltered
  12. customthe solvent was removed in vacuo
  13. custom38.25 g of light yellow-orange oil were obtained
  14. customThis product was used without any further purification

Sources & evidence

ORD record
ord-c4d999e1865444fe9db2432508967175
Source dataset
uspto-grants-2002_05
Patent number
US06391991B1

Reaction notes

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