P-Anisidine → HCID 14499218, compound

HRID 1194502Notes

Reaction equation

HRID 1194502 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH:10]1[CH2:11][CH:12]=[CH:13][C:14]2[C:19]=1[CH:18]=[CH:17][CH2:16][CH:15]=2.S(=O)(O)[O-:21].[Na+]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:12]2[CH:13]=[C:14]3[C:19](=[CH:10][CH:11]=2)[CH:18]=[C:17]([OH:21])[CH:16]=[CH:15]3)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 144992172,6-DihydronaphthaleneHCID 23665763Sodium Bisulfite

Product 1

HCID 14499218HCID 14499218, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.00 g (8.1 mmol, Aldrich) of p-anisidine, 5.20 g (32.5 mmol, 4 eq., Aldrich) of 2,6-dihydronaphthalene and 3.38 g (32.5 mmol, 4 eq., Aldrich) of sodium bisulfite in 60 ml of H2O was refluxed for 12 hours. The reaction was cooled to room temperature, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo. Initial purification was accomplished via flash chromatography (1:6, 1:4 EtOAc/petroleum ether) and then concentration of appropriate fractions. Ethyl acetate was added, this was washed repeatedly with warm 0.1N NaOH to remove 2,6-dihydroxynaphthalene, dried (MgSO4) and concentrated in vacuo. Final purification by flash chromatography (1:4 THF/petroleum ether) yielded 633 mg (30%) of title compound as a muddy pink solid, m.p. 152°-153° C.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customInitial purification
  5. additionEthyl acetate was added
  6. washthis was washed repeatedly
  7. temperaturewith warm 0.1N NaOH
  8. customto remove 2,6-dihydroxynaphthalene
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customFinal purification by flash chromatography (1:4 THF/petroleum ether)

Sources & evidence

ORD record
ord-5736afd81bb8428c8cc0b80e5d785e8f
Source dataset
uspto-grants-1989_03
Patent number
US04814454

Reaction notes

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