Resorcinol → HCID 10844720, compound

HRID 1904536Notes

Reaction equation

HRID 1904536 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].CO[CH:11]([CH3:15])[C:12](=O)[CH3:13]>C1(C)C=CC=CC=1>[CH3:15][C:11]1[O:2][C:1]2[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=2[C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 5054ResorcinolHCID 125005003-Methoxybutan-2-one

Product 1

HCID 10844720HCID 10844720, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.9 g of resorcinol, 1.8 g of 3-methoxy-2-butanone, 0.2 g of Amberlyst-15 and 2 ml of toluene was stirred at 90° C. for 10 hours. After cooling, the catalyst was separated, and the filtrate was concentrated. The residue was purified by column chromatography to give 1.7 g of 2,3-dimethyl-6-hydroxybenzofuran as pale yellow crystals. The crystals were dissolved in 20 ml of acetic acid, and 0.2 g of 5% palladium-carbon was added. The mixture was stirred at room temperature for 12 hours in an atmosphere of hydrogen. The crude product was purified by column chromatography to give 1.5 g (yield 54%) of the desired product as a brown liquid.

Workup

  1. temperatureAfter cooling
  2. customthe catalyst was separated
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b62fb8b8690e4f6baf4290488facc732
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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