6-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)-6-(4-methoxyphenyl)hexanoic acid → 6-(3-Methyl-1,4-naphthoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acid

HRID 2393185Notes

Reaction equation

HRID 2393185 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13]C)=[C:5]([CH3:15])[C:4]=1[CH:16]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]>C(#N)C>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([CH:16]([C:4]2[C:3](=[O:2])[C:12]3[C:7]([C:6](=[O:13])[C:5]=2[CH3:15])=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 189792506-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)-6-(4-methoxyphenyl)hexanoic acid

Product 1

HCID 152308586-(3-Methyl-1,4-naphthoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 14.7 g of 6-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)-6-(4-methoxyphenyl)hexanoic acid in 300 ml of acetonitrile at 0C was added an aqueous 147 ml solution of 57.2 g of ceric ammonium nitrate portionwisely over 5 min. After stirring for 16 hours at room temperature, the solution was extracted with ethyl acetate. The organic layer was washed, dried, evaporated, and the residue was purified with column chromatography over silica gel using ethyl acetate as an eluent. Recrystallization from isopropyl ether/ethyl acetate gave 10.8 g of the title compound.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried
  4. customevaporated
  5. customthe residue was purified with column chromatography over silica gel
  6. customRecrystallization from isopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-f527d0de9477491f9d059aa47583a799
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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