Hydrochloric Acid → 3,5,6,7-tetrahydro-s-indacen-1(2H)-one

HRID 888321Notes

Reaction equation

HRID 888321 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[CH2:11][CH2:12][C:13](Cl)=[O:14].[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:13]1(=[O:14])[C:7]2[C:6](=[CH:5][C:4]3[CH2:3][CH2:2][CH2:1][C:9]=3[CH:8]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10326IndaneHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 109318913,5,6,7-tetrahydro-s-indacen-1(2H)-oneYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of 11.8 g indane (0.1 mol) and 10 ml 3-chloropropionyl chloride (0.12 mol) was added to suspension of 16 g AlCl3 (0.55 mol) in 100 ml CH2Cl2 at 0° C. After then reaction mixture was poured into ice and HCl, the organic layer was isolated; the aqueous one was extracted with CH2Cl2 (2*50 ml). The combined organic phase was washed by NaHCO3, dried over MgSO4 and evaporated. The residue was added carefully to conc. H2SO4 (100 ml), warmed to 70° C. and stirred after then 30 min at the same temperature. The mixture was cooled and poured into ice. Precipitate was filtered, washed by water and dried, to give 12.4 g of product (72%).

Workup

  1. customAfter then reaction mixture
  2. customthe organic layer was isolated
  3. extractionthe aqueous one was extracted with CH2Cl2 (2*50 ml)
  4. washThe combined organic phase was washed by NaHCO3
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. additionThe residue was added carefully to conc. H2SO4 (100 ml)
  8. temperatureThe mixture was cooled
  9. additionpoured into ice
  10. filtrationPrecipitate was filtered
  11. washwashed by water
  12. customdried

Sources & evidence

ORD record
ord-1034cf5ac099433cbbf7dee74cd83269
Source dataset
uspto-grants-2012_08
Patent number
US08247587B2

Reaction notes

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