Pyridinium chloride → 5,6-dichloro-9a-ethyl-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 1157026Notes

Reaction equation

HRID 1157026 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16]C)[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:18][CH3:19])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:20])[CH:5]=1.Cl.N1C=CC=CC=1>O>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([OH:16])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:18][CH3:19])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:20])[CH:5]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 128069345,6-dichloro-9a-ethyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 128069355,6-dichloro-9a-ethyl-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5,6-Dichloro-9a-ethyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (15 gm., 0.048 mole) is mixed with pyridine hydrochloride (120 gm.) in a reaction vessel and heated in a metal bath at 195°-200° C. for 30 minutes. The mixture is cooled somewhat and poured with stirring into cold water (800 ml.). The solid that separates is removed by filtration and washed with water. After drying, the product is triturated with acetonitrile (80 ml.) at 60°, cooled, filtered and dried. The yield of crude 5,6-dichloro-9a-ethyl-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one is 12.2 gm., m.p. 260°-265° C. This material is pure enough for use in the next step.

Workup

  1. temperatureheated in a metal bath at 195°-200° C. for 30 minutes
  2. temperatureThe mixture is cooled somewhat
  3. additionpoured
  4. customThe solid that separates is removed by filtration
  5. washwashed with water
  6. customAfter drying
  7. customthe product is triturated with acetonitrile (80 ml.) at 60°
  8. temperaturecooled
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-5ebab82be93a45a0947e177b93f03e4a
Source dataset
uspto-grants-1982_06
Patent number
US04337354

Reaction notes

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