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

HRID 222481

Reaction equation

HRID 222481 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)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methacryloyl chloride (50 ml, 0.5 mol) was added to suspension of 133.5 r AlCl3 (1 mol) in 500 ml CH2Cl2 at −78° C., stirred 20 min. Then indane (59 g, 0.5 mol) was added at the same temperature, allowed to warm to room temperature and then was stirred overnight. Next day the mixture obtained was poured carefully into mixture of ice (1000 g) and HCl (200 ml). The organic phase was separated, washed by water, 5% NaHCO3, and dried over MgSO4. Solvent was evaporated and residue was distilled in vacuum given 77.6 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 by water, 5% NaHCO3
  5. dry with materialdried over MgSO4
  6. customSolvent was evaporated
  7. distillationresidue was distilled in vacuum

Sources & evidence

ORD record
ord-75ec45925fb84254861ee6335275f203
Source dataset
uspto-grants-2012_06
Patent number
US08207269B2

Linked notes

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