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

HRID 888320Notes

Reaction equation

HRID 888320 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.Cl>C(Cl)Cl>[CH3:3][CH:2]1[CH2:4][C:17]2[C:16](=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][C:19]=3[CH:18]=2)[C:1]1=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10326IndaneHCID 13528Methacryloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 109542593,5,6,7-Tetrahydro-2-methyl-s-indacen-1(2H)-oneYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methacryloyl chloride (50 ml, 0.5 mol) was added to a suspension of 133.5 g (1 mol) AlCl3 in 500 ml CH2Cl2 at −78° C. and stirred for 20 min. Then 59 g (0.5 mol) indane was added at the same temperature. The mixture was allowed to warm to room temperature and then was stirred overnight. Next day the mixture obtained was poured carefully into a mixture of ice (1000 g) and HCl (200 ml). The organic phase was separated, washed with water and 5% NaHCO3, and dried over MgSO4. Solvent was evaporated and residue was distilled in vacuum giving 77.6 g of product (83%), b.p. 118-120° C./0.5 torr.

Workup

  1. stirringwas stirred overnight
  2. customNext day the mixture obtained
  3. customThe organic phase was separated
  4. washwashed with water and 5% NaHCO3
  5. dry with materialdried over MgSO4
  6. customSolvent was evaporated
  7. distillationresidue was distilled in vacuum

Sources & evidence

ORD record
ord-2a42855ca1464ae8bf5191ba4049d345
Source dataset
uspto-grants-2012_08
Patent number
US08247587B2

Reaction notes

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