Hydrochloric Acid → 6-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-ol

HRID 748962Notes

Reaction equation

HRID 748962 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.Br[C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[C:8]([C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1)[CH:7]=[CH:6]2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 141126-Methoxy-alpha-tetraloneHCID 660374-BromothioanisoleHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 685188176-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-ol

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Place 6-methoxy-1-tetralone (1 eq.), 4-bromothioanisole (2.5 eq.), palladium acetate (0.01 eq.), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.02 eq.) and toluene in a 3 neck flask equipped with a mechanical stirrer, reflux condenser, nitrogen purge and a temperature probe. Add sodium tert-butoxide (4 eq.) and heat the slurry to reflux. After about 2-4 hours, cool the reaction to room temperature and add 3M aqueous HCl along with tetrahydrofuran. Stir the biphasic reaction mixture for 30 minutes before filtration and separation of the layers. Concentrate the organic layer to isolate 6-methoxy-2-(4-methylthiophenyl)naphthalene-1-ol by filtration.

Workup

  1. temperaturereflux condenser
  2. customnitrogen purge
  3. temperatureto reflux
  4. temperaturecool
  5. customthe reaction to room temperature
  6. customthe biphasic reaction mixture for 30 minutes
  7. filtrationbefore filtration and separation of the layers
  8. concentrationConcentrate the organic layer

Sources & evidence

ORD record
ord-ae155ea000984dd195ac0aaddec3f248
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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