p-Toluenesulfonic acid → HCID 67972743, compound

HRID 1408275Notes

Reaction equation

HRID 1408275 reaction equation
C1(C2C=CC=CC=2)C=CC([C:7]2[C:16]3[C:11](=[C:12]([O:17][CH3:18])[CH:13]=[CH:14][CH:15]=3)[C:10]([OH:19])=[CH:9][C:8]=2[C:20](O)([CH3:22])[CH3:21])=CC=1.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33](S(O)(=O)=O)=[CH:32][CH:31]=1>C(OC)(C)(C)C>[CH3:18][O:17][C:12]1[C:11]2[C:10]([OH:19])=[CH:9][C:8]3[C:20]([CH3:22])([CH3:21])[C:32]4[CH:31]=[C:30]([C:40]5[CH:15]=[CH:16][CH:7]=[CH:8][CH:9]=5)[CH:35]=[CH:34][C:33]=4[C:7]=3[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67972739HCID 67972739, compound

Product 1

HCID 67972743HCID 67972743, compoundYield 569.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

In an oven-dried flask placed under a nitrogen atmosphere and equipped with a Dean-Stark trap, the product of Step 5 (20 g) was stirred in xylenes (300 mL). To this was added p-toluenesulfonic acid (990 mg). The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. It was transferred to a separatory funnel and washed with saturated aqueous solution of sodium bicarbonate (300 mL), dried over sodium sulfate and then concentrated by rotary evaporation to yield a solid. The solid was slurried in a minimal amount of methyl tert-butyl ether and collected by vacuum filtration yielding 12 g of 4-methoxy-7,7-dimethyl-9-phenyl-7H-benzo[C]fluoren-5-ol.

Workup

  1. customIn an oven-dried flask placed under a nitrogen atmosphere
  2. customequipped with a Dean-Stark trap
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 3 hours
  5. customIt was transferred to a separatory funnel
  6. washwashed with saturated aqueous solution of sodium bicarbonate (300 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated by rotary evaporation
  9. customto yield a solid
  10. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-ca4e962e3edf477aa41c02cc646c640b
Source dataset
uspto-grants-2014_12
Patent number
US08920928B2

Reaction notes

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