Ammonium Chloride → (4-Hydroxyphenyl)(2-phenyl-3,4-dihydronaphthalen-1-yl)methanone

HRID 904334Notes

Reaction equation

HRID 904334 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:16]=2[C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-]CC.[Na+].[Cl-].[NH4+]>CN(C=O)C>[C:1]1([C:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:16]=2[C:17](=[O:26])[C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4459711Sodium ethanethiolateHCID 12835030(4-Methoxyphenyl)(2-phenyl-3,4-dihydronaphthalen-1-yl)methanone

Product 1

HCID 15383364(4-Hydroxyphenyl)(2-phenyl-3,4-dihydronaphthalen-1-yl)methanoneYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To 2.0 grams (0.006 mole) of the above dihydronaphthalene dissolved in 10 ml. of N,N-dimethyl formamide were added 7.5 mmoles of sodium thioethoxide in 15 ml. of DMF. The addition was carried out under a nitrogen atmosphere and at 80° C. The mixture was maintained at 80° C. for fifteen hours. The mixture then was cooled and poured into an iced aqueous ammonium chloride solution. The resulting mixture was extracted with ethyl acetate, and the ethyl acetate extract was washed four times with aqueous sodium chloride solution. The ethyl acetate then was dried over magnesium sulfate and evaporated to give an oil which was chromatographed rapidly over a 2"×2" silica column using benzene to elute impurities. The product then was eluted with ethyl acetate to give, upon evaporation of the ethyl acetate, 1.69 grams (88%) of 3-phenyl-4-(4-hydroxybenzoyl)-1,2-dihydronaphthalene as a clear pale yellow oil.

Workup

  1. additionThe addition
  2. customwas carried out under a nitrogen atmosphere and at 80° C
  3. temperatureThe mixture then was cooled
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. extractionthe ethyl acetate extract
  6. washwas washed four times with aqueous sodium chloride solution
  7. dry with materialThe ethyl acetate then was dried over magnesium sulfate
  8. customevaporated
  9. customto give an oil which
  10. customwas chromatographed rapidly over a 2"×2" silica column
  11. washto elute impurities
  12. washThe product then was eluted with ethyl acetate

Sources & evidence

ORD record
ord-b17b5e47423b4586af98dda848da5caf
Source dataset
uspto-grants-1980_10
Patent number
US04230862

Reaction notes

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