p-Toluenesulfonic acid monohydrate → HCID 15157221, compound

HRID 2051422Notes

Reaction equation

HRID 2051422 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:19])=[C:7]2[C:15]=1[C:14](=[CH:16][O:17]C)[CH:13]1[CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.O>[CH:16]([CH:14]1[CH:13]2[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]2)[C:7]2[C:15]1=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[CH3:19])=[O:17]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 54308991HCID 54308991, compound

Product 1

HCID 15157221HCID 15157221, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4.54 Grams of 8-methoxy-9-methoxymethylene-5-methyl-1,2,3,4,4a,9a-hexahydrofluorene was dissolved in 200 ml of 1,4-dioxane and 50 ml of water. To the solution was added 0.90 g of p-toluenesulfonic acid monohydrate and this was refluxed for 18 hours. To the reaction mixture was added 200 ml of water and extraction was carried out with diethyl ether. The organic layer was dried with magnesium sulfate, filtered and concentrated and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10) and recrystallized from ethanol to obtain 3.94 g of 9-formyl-8-methoxy-5-methyl-1,2,3,4,4a,9a-hexahydrofluorene having a melting point of 92°-93° C. and of colorless needle-like crystal.

Workup

  1. temperaturethis was refluxed for 18 hours
  2. additionTo the reaction mixture was added
  3. extraction200 ml of water and extraction
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-89f19afc2388464c9978ab2ea5491dd8
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

Loading…