Water → 9a-Acetyl-1,2,3,4,4a,9a-hexahydrofluoren-9-one

HRID 279146Notes

Reaction equation

HRID 279146 reaction equation
[CH2:1]1[CH:13]2[CH:5]([C:6]3[C:11]([C:12]2=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][CH2:2]1.[C:15]1([CH3:25])C=CC(S(O)(=O)=O)=CC=1.[OH2:26]>C(OC(=O)C)(=O)C>[C:15]([C:11]12[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[C:5]1[C:13](=[CH:1][CH:2]=[CH:3][CH:4]=1)[C:12]2=[O:14])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6041812,3,4,4a-Tetrahydro-1H-fluoren-9(9aH)-one

Product 1

HCID 226245739a-Acetyl-1,2,3,4,4a,9a-hexahydrofluoren-9-one

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

1,2,3,4,4a,9a-Hexahydrofluoren-9-one (9.6 g) was dissolved in acetic anhydride (40 ml). p-Toluenesulfonic acid (1 g) was added and the mixture was refluxed for 1 hour. The mixture was cooled in an ice bath and water (20 ml) was added. After stirring for 20 minutes solvent was removed with an evaporator. The residue was dissolved in ethyl acetate (60 ml) and extracted with 5% NaHCO3 solution (2×30 ml) and water (30 ml). The organic phase was dried over Na2SO4 and evaporated. Yield was 10.9 g.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureThe mixture was cooled in an ice bath
  3. customwas removed with an evaporator
  4. dissolutionThe residue was dissolved in ethyl acetate (60 ml)
  5. extractionextracted with 5% NaHCO3 solution (2×30 ml) and water (30 ml)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-d319a0a5a2fc484d94ec9b3b85b624bd
Source dataset
uspto-grants-2002_03
Patent number
US06362211B1

Reaction notes

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