Hydrochloric Acid → HCID 178458818, compound

HRID 1195457Notes

Reaction equation

HRID 1195457 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH2:12][CH2:11]3)[CH2:5][C:4](=[O:17])[CH:3]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26].[Cl-].[Cl-].[Cl-].[Al+3].Cl>ClCCl.ClCCCl.O>[OH:17][C:4]1[CH2:5][CH:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH2:12][CH2:11]3)[CH2:7][C:2](=[O:1])[C:3]=1[C:24](=[O:27])[CH2:25][CH3:26]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 137335195-(2,3-Dihydro-1H-inden-5-yl)-3-hydroxycyclohex-2-en-1-one

Product 1

HCID 178458818HCID 178458818, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-hydroxy-5-(5-indanyl)cyclohex-2-en-1-one (5.0 g; 22 mmole) in dichloromethane (100 ml) and pyridine (1.74 g; 22 mmole) was stirred at room temperature whilst propionyl chloride (1.92 g; 22 mmole) was added dropwise over a period of two minutes. Stirring was continued for 1 hour after which the organic solution was washed with water (2×100 ml), dried over anhydrous sodium sulphate, and the solvent was removed under reduced pressure using a rotary evaporator. The resulting brown oil was immediately dissolved in 1,2-dichloroethane (50 ml) and added dropwise to a mixture of aluminium trichloride (5.85 g; 44 mmole) in 1,2-dichloroethane (50 ml) over 30 min at such a rate that the temperature did not exceed 30° C. After stirring for 30 min at room temperature, the solution was poured into 100 ml of a 1:1 mixture of concentrated hydrochloric acid and water. The organic solution was washed with water (2×200 ml), dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure using a rotary evaporator. The resulting yellow oil was purified by chromatography over silica gel (eluant dichloromethane) to give 3-hydroxy-5-(5-indanyl)-2-propionylcyclohex-2-en-1-one, (1.71 g; 27%) as a yellow solid, mp 98° C.

Workup

  1. additionwas added dropwise over a period of two minutes
  2. washafter which the organic solution was washed with water (2×100 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customthe solvent was removed under reduced pressure
  5. customa rotary evaporator
  6. dissolutionThe resulting brown oil was immediately dissolved in 1,2-dichloroethane (50 ml)
  7. customdid not exceed 30° C
  8. stirringAfter stirring for 30 min at room temperature
  9. washThe organic solution was washed with water (2×200 ml)
  10. dry with materialdried over anhydrous sodium sulphate
  11. customthe solvent was removed under reduced pressure
  12. customa rotary evaporator
  13. customThe resulting yellow oil was purified by chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-30635f148cac4720a212d6f8cfcba8cb
Source dataset
uspto-grants-1992_05
Patent number
US05110989

Reaction notes

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