Pyridinium chloride → 2-Butyl-6,7-dichloro-2-cyclopentyl-5-hydroxy-1-indanone

HRID 1463136Notes

Reaction equation

HRID 1463136 reaction equation
Cl.N1C=CC=CC=1.[CH2:8]([C:12]1([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:20][C:19]2[C:14](=[C:15]([Cl:24])[C:16]([Cl:23])=[C:17]([O:21]C)[CH:18]=2)[C:13]1=[O:25])[CH2:9][CH2:10][CH3:11]>CCOCC>[CH2:8]([C:12]1([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:20][C:19]2[C:14](=[C:15]([Cl:24])[C:16]([Cl:23])=[C:17]([OH:21])[CH:18]=2)[C:13]1=[O:25])[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 127611342-Butyl-6,7-dichloro-2-cyclopentyl-5-methoxy-1-indanone

Product 1

HCID 127611362-Butyl-6,7-dichloro-2-cyclopentyl-5-hydroxy-1-indanoneYield 86.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
190 °C

Procedure

To pyridine hydrochloride (50 g) fused at 190° C. was added 2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-1H-inden-1-one (6.6 g). The reaction mixture was stirred at 190° C. in an inert atmosphere for 11/2 hours then poured onto ice water. The resulting solid was dissolved in ether, washed with water, dried over MgSO4, evaporated at reduced pressure then triturated with hexane (50 ml) to give 5.5 g of 2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-5-hydroxy-1H-inden-1-one, m.p. 159.5°-160° C.

Workup

  1. customfused at 190° C.
  2. additionthen poured onto ice water
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customevaporated at reduced pressure
  6. customthen triturated with hexane (50 ml)

Sources & evidence

ORD record
ord-b631a3c4b5af418e88374f0e40de3227
Source dataset
uspto-grants-1984_07
Patent number
US04463208

Reaction notes

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