Ammonium Chloride → HCID 86737299, compound

HRID 904336Notes

Reaction equation

HRID 904336 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[CH2:11]([O:18][C:19]1[CH:39]=[CH:38][C:22]([C:23]([CH:25]2[C:34]3[C:29](=[CH:30][C:31]([O:35][CH3:36])=[CH:32][CH:33]=3)[CH2:28][CH2:27][C:26]2=O)=[O:24])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:28]2[C:29]3[C:34](=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)[C:25]([C:23](=[O:24])[C:22]3[CH:38]=[CH:39][C:19]([O:18][CH2:11][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)=[CH:20][CH:21]=3)=[CH:26][CH2:27]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 20491205HCID 20491205, compoundHCID 178491912HCID 178491912, compound

Product 1

HCID 86737299HCID 86737299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of about 50 grams (0.24 mole) of p-methoxyphenylmagnesium bromide in tetrahydrofuran (THF) were added at room temperature 30.2 grams (0.08 mole) of 1-(p-benzyloxybenzoyl)-6-methoxy-2-tetralone dissolved in THF. Upon completion of the addition, the entire mixture was warmed to 45° C. Analysis of a sample of the mixture by thin-layer chromatography (TLC) showed the absence of starting material. The mixture then was poured into aqueous ammonium chloride solution, and the resulting mixture was extracted with ethyl acetate. The ethyl acetate extract was washed, dried, and evaporated. The resulting residue was dissolved in benzene, and a catalytic amount of p-toluenesulfonic acid was added. The mixture was stirred at room temperature until a TLC of the mixture indicated the absence of any carbinol intermediate. The mixture then was washed with water, dried, and concentrated. The residue was chromatographed over one kg. of alumina using 6 l. of benzene. The product was eluted with a mixture of 2 percent ethyl acetate in benzene. The product, 3-(4-methoxyphenyl-4-(4-benzyloxybenzoyl)-7-methoxy-1,2-dihydronaphthalene was obtained as an oil.

Workup

  1. additionUpon completion of the addition
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed
  5. customdried
  6. customevaporated
  7. dissolutionThe resulting residue was dissolved in benzene
  8. additiona catalytic amount of p-toluenesulfonic acid was added
  9. washThe mixture then was washed with water
  10. customdried
  11. concentrationconcentrated
  12. customThe residue was chromatographed over one kg
  13. washThe product was eluted with a mixture of 2 percent ethyl acetate in benzene

Sources & evidence

ORD record
ord-229d39f536cc42418c394d4cb62b8ec9
Source dataset
uspto-grants-1980_10
Patent number
US04230862

Reaction notes

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