Pyridinium chloride → 3,4-Dichloro-6,7,8,8a,9,10-hexahydro-2-hydroxy-6-oxo-8a-propylphenanthrene

HRID 867995Notes

Reaction equation

HRID 867995 reaction equation
Cl.N1C=CC=CC=1.[Cl:8][C:9]1[C:10]([O:28]CC(O)=O)=[CH:11][C:12]2[CH2:13][CH2:14][C:15]3([CH2:25][CH2:26][CH3:27])[C:20]([C:21]=2[C:22]=1[Cl:23])=[CH:19][C:18](=[O:24])[CH2:17][CH2:16]3>>[Cl:8][C:9]1[C:10]([OH:28])=[CH:11][C:12]2[CH2:13][CH2:14][C:15]3([CH2:25][CH2:26][CH3:27])[C:20]([C:21]=2[C:22]=1[Cl:23])=[CH:19][C:18](=[O:24])[CH2:17][CH2:16]3

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 21289572[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetic acid

Product 1

HCID 212895743,4-Dichloro-6,7,8,8a,9,10-hexahydro-2-hydroxy-6-oxo-8a-propylphenanthrene

Conditions

Temperature
190 °C

Procedure

Pyridine hydrochloride (20 g, 173 mmole) is melted and heated to 190° C. and then (-) [(3,4-dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetic acid (Example 3) (325 mg, 1 mmole) is added and stirred for 15 minutes at 190°. The mixture is poured into crushed ice (200 g) and the product extracted with ether. The organic extract is washed with water, then with brine and dried over MgSO4. Evaporation of the solvent gave (-)3,4-dichloro-6,7,8,8a,9,10-hexahydro-2-hydroxy-6-oxo-8a-propylphenanthrene.

Workup

  1. additionThe mixture is poured
  2. extractionthe product extracted with ether
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialwith brine and dried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6e5d09f047a84d7e97034c1665a36b51
Source dataset
uspto-grants-1988_10
Patent number
US04777281

Reaction notes

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