HCID 19088067, compound → HCID 19088054, compound

HRID 1464526Notes

Reaction equation

HRID 1464526 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][CH2:21][CH2:22][OH:23]>C(O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH:14]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23]

Participants

4

Reactant 1

HCID 19088067HCID 19088067, compound

Product 1

HCID 19088054HCID 19088054, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5% Palladium-carbon (0.2 g) was added to a solution of 1.970 g (5.0 mmole) of 9-(2,5-dimethoxy-3,4,6-trimethylphenyl)-9-phenyl-3-nonyn-1-ol in ethanol (20 ml), and catalytic reduction was conducted at room temperature for 2 hours. The catalyst was filtered out, and the ethanol was distilled off under reduced pressure. The residue was chromatographed on a silica gel column to perform purification (elution with isopropyl ether) to thereby give 1.97 g (99%) of 9-(2,5-dimethoxy-3,4,6-trimethylphenyl)-9-phenylnonanol. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 14.

Workup

  1. filtrationThe catalyst was filtered out
  2. distillationthe ethanol was distilled off under reduced pressure
  3. customThe residue was chromatographed on a silica gel column
  4. custompurification (elution with isopropyl ether)

Sources & evidence

ORD record
ord-94d46d08f88f4b80b45a826365ae9a05
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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