HCID 11065315, compound → HCID 14672089, compound

HRID 2254196Notes

Reaction equation

HRID 2254196 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH3:14])[CH:5]=[C:4]([O:15][CH3:16])[C:3]=1[C:17](=[O:19])[CH3:18].[H][H]>C(OCC)(=O)C>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH3:14])[CH:5]=[C:4]([O:15][CH3:16])[C:3]=1[C:17](=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 11065315HCID 11065315, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14672089HCID 14672089, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An ethyl acetate solution of 22.2 g of 2'-hydroxy-4',6'-dimethoxy-3'-(3-methyl-2-butenyl)acetophenone was added into a sufficiently hydrogen gas-absorbed suspension of 1.5 g of 5% palladium-carbon in 20 ml of ethyl acetate, and the mixture was stirred at room temperature for 2 hours in a hydrogen gas atmosphere. After the reaction, the reaction mixture was filtered and the solvent was removed by distillation. The residue was recrystallized from n-hexane to obtain 20.4 g (yield=91.2%) of 2'-hydroxy-3'-isopentyl-4',6'-dimethoxyacetophenone in the form of a colorless needle.

Workup

  1. customgas-absorbed
  2. additionsuspension of 1.5 g of 5% palladium-carbon in 20 ml of ethyl acetate
  3. customAfter the reaction
  4. filtrationthe reaction mixture was filtered
  5. customthe solvent was removed by distillation
  6. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-4920328d565942c89a5f38986cfd176e
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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