Ammonium Chloride → p-(6-Methoxy-2-phenyl-3,4-dihydro-1-naphthyl)phenol

HRID 1926577Notes

Reaction equation

HRID 1926577 reaction equation
C(O[K])(C)(C)C.[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]([C:25]3[CH:30]=[CH:29][C:28]([O:31]C(=O)C(C)(C)C)=[CH:27][CH:26]=3)[CH:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:15]=[CH:16]2)=[CH:11][CH:10]=1.[Cl-].[NH4+]>CS(C)=O>[OH:31][C:28]1[CH:27]=[CH:26][C:25]([C:13]2[C:12]3[C:17](=[CH:18][C:9]([O:8][CH3:7])=[CH:10][CH:11]=3)[CH2:16][CH2:15][C:14]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 575434947-Methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-3,4-dihydronaphthaleneHCID 178418922HCID 178418922, compound

Product 1

HCID 200362p-(6-Methoxy-2-phenyl-3,4-dihydro-1-naphthyl)phenolYield 69%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a dimethyl sulfoxide (0.6 mL) solution of tertiary butoxy potassium (40.3 mg, 0.359 mmol), a dimethyl sulfoxide (0.8 mL) solution of 7-methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-3,4-dihydronaphthalene (6, 29.3 mg, 0.0710 mmol) was added, and stirred at room temperature for one day and night. After adding saturated ammonium chloride (10 mL) to the reaction mixture with much stirring, extraction was carried out three times with diethyl ether. The organic layers were combined, washed with a saturated sodium chloride solution (10 mL), and after drying with anhydrous sodium sulphate, concentrated. The residue was purified with thin layer chromatography (toluene:ethyl acetate=10:1), to obtain the subject compound (7, 16.0 mg; yield=69%).

Workup

  1. extractionwith much stirring, extraction
  2. washwashed with a saturated sodium chloride solution (10 mL)
  3. dry with materialafter drying with anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified with thin layer chromatography (toluene:ethyl acetate=10:1)
  6. customto obtain the subject compound (7, 16.0 mg; yield=69%)

Sources & evidence

ORD record
ord-e271fb3a49d840d492d2df129b62b66b
Source dataset
uspto-grants-2012_05
Patent number
US08183235B2

Reaction notes

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