1-Naphthol → 7,8,9,10-Tetrahydrobenzo[b]naphtho[2,1-d]furan

HRID 539257Notes

Reaction equation

HRID 539257 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O.[C:13]1(C)[CH:18]=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.C1CCC=CC=1>C1(C)C=CC=CC=1>[CH:9]1[C:10]2[C:1]3[O:11][C:14]4[CH2:15][CH2:16][CH2:17][CH2:18][C:13]=4[C:2]=3[CH:3]=[CH:4][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 116051,3-CyclohexadieneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 2685557,8,9,10-Tetrahydrobenzo[b]naphtho[2,1-d]furanYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

144 g of 1-naphthol, 190 g of p-toluenesulfonic acid monohydrate, 80.1 g of 1,3-cyclohexadiene and 4 L of toluene were placed in a flask. The resulting mixture was stirred under reflux for 24 hours. After cooling to room temperature, the reaction solution was washed with 600 mL of water. After drying an organic phase with magnesium sulfate, the solvent was distilled off under reduced pressure. Residues were purified by silica gel column chromatography, whereby 55.5 g (yield: 25%) of 7,8,9,10-tetrahydrobenzo[b]naphtho[2,1-d]furan was obtained.

Workup

  1. temperatureunder reflux for 24 hours
  2. washthe reaction solution was washed with 600 mL of water
  3. dry with materialAfter drying an organic phase with magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customResidues were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-44d7afc00dd5450a820309ce46f08466
Source dataset
uspto-grants-2014_10
Patent number
US08866135B2

Reaction notes

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