HCID 14579790, compound → HCID 14579778, compound

HRID 1607270Notes

Reaction equation

HRID 1607270 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH2:20][CH:21]=[CH2:22])[C:12]=3[C:13]=2[CH3:14])=O)=[CH:5][CH:4]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH2:20][CH2:21][CH3:22])[C:12]=3[C:13]=2[CH3:14])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 14579790HCID 14579790, compound

Product 1

HCID 14579778HCID 14579778, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(p-methoxybenzoyl)-3-methyl-4-allyl-5-hydroxybenzofuran (3 gm, 9.3 mmoles) in ethanol (150 mL) was hydrogenated in a Parr hydrogenator in the presence of 10% palladium on charcoal at 40 psi for a period of 3 hours. The catalyst was filtered off, washed with some ethanol, and the filtrate was concentrated in vacuo. The residue was recrystallized from hexane to yield (1.1 gm, 38%) of 2-(p-methoxybenzyl)-3-methyl-4-propyl-5-hydroxybenzofuran, mp. 91°-93° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with some ethanol
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-d5980ba752d548229c133f74f4fda63b
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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