Hydrochloric Acid → 2,3,4,9-Tetrahydro-1H-fluorene

HRID 1279900Notes

Reaction equation

HRID 1279900 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>CCCCCC>[CH2:17]1[C:12]2[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:13]=2[CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 989452-Benzylcyclohexan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5884652,3,4,9-Tetrahydro-1H-fluoreneYield 23%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

Aluminium chloride (53.7 g, 0.40 mol) was added portion wise to 2-benzylcyclohexanone (25 g, 0.13 mol) in 100 mL of hexane. The mixture was heated at 60° C. for 4 h then cooled and poured onto ice acidified with HCl (aq). The organic layer was decanted and the aqueous layer was extracted with 100 mL of hexane. The organics were washed once with a dilute HCl solution, a dilute sodium bicarbonate solution and finally with water. The organic layer was dried, filtered and the hexane was removed. The resulting oil was distilled at 110-135° C. at 4 mm Hg, followed by crystallization from methanol gave (5 g, 23%) of tetrahydrofluorene as a white solid, mp 57° C.

Workup

  1. temperaturethen cooled
  2. additionpoured onto ice
  3. customThe organic layer was decanted
  4. extractionthe aqueous layer was extracted with 100 mL of hexane
  5. washThe organics were washed once with a dilute HCl solution
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customthe hexane was removed
  9. distillationThe resulting oil was distilled at 110-135° C. at 4 mm Hg
  10. customfollowed by crystallization from methanol

Sources & evidence

ORD record
ord-7a1735e338fc4e1387e88684a388464f
Source dataset
uspto-grants-2002_09
Patent number
US06448424B1

Reaction notes

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