HCID 19088046, compound → HCID 15230860, compound

HRID 1464497Notes

Reaction equation

HRID 1464497 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11]C)=[C:5]([CH3:13])[C:4]=1[CH:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]>C(#N)C.O>[CH3:13][C:5]1[C:6](=[O:11])[C:7]([CH3:10])=[C:8]([CH3:9])[C:3](=[O:2])[C:4]=1[CH:14]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]

Participants

4

Reactant 1

HCID 19088046HCID 19088046, compound

Product 1

HCID 15230860HCID 15230860, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

7-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptanol (1.85 g, 5.0 mmole) was dissolved in a mixed solution of acetonitrile (12 ml) and water (6 ml), and a cooled solution of ceric ammonium nitrate (8.22 g, 5×3 mmole) in 50% aqueous acetonitrile (16 ml) was added dropwise to the solution, under ice cooling, over the 20-minutes period. After stirring was continued for another 20 minutes under ice cooling, acetonitrile was distilled off under reduced pressure, and isopropyl ether was added to the residue to conduct extraction. The isopropyl ether layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate), and evaporated. The residual solution was chromatographed on a silica gel column, and purification was performed (elution with isopropyl ether) to give 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanol (1.53 g, 90%). Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 1. By following the procedure of this Example, the Compound Nos. 9, 10, 35, 36, 46 to 55 and 64 to 67 were prepared.

Workup

  1. distillationacetonitrile was distilled off under reduced pressure, and isopropyl ether
  2. additionwas added to the residue
  3. extractionextraction
  4. customThe isopropyl ether layer was separated out
  5. washwashed with aqueous sodium chloride solution
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated
  8. customThe residual solution was chromatographed on a silica gel column, and purification
  9. wash(elution with isopropyl ether)

Sources & evidence

ORD record
ord-1e6aa59225ef48de9d7bf78044c9d255
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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