Hydrazine → 2-(p-Methoxybenzyl)-3-methyl-4-hydroxybenzofuran

HRID 1607272Notes

Reaction equation

HRID 1607272 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:12]=3[C:13]=2[CH3:14])=O)=[CH:5][CH:4]=1.NN.[OH-].[K+]>C(O)CO.O>[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][CH:16]=[C:15]([OH:19])[C:12]=3[C:13]=2[CH3:14])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 145797912-(p-Methoxybenzoyl)-3-methyl-4-hydroxybenzofuran

Product 1

HCID 145708882-(p-Methoxybenzyl)-3-methyl-4-hydroxybenzofuranYield 37,270.699%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of 2-(p-methoxybenzoyl)-3-methyl-4-hydroxybenzofuran (2.0 gm; 7.0 mmoles), 99% hydrazine (50 mL) and potassium hydroxide (2.7 gm; 49 mmoles) in ethylene glycol (50 mL) was heated at 140° C. for a period of 2.5 hours and at 195° C. for one hour. The reaction mixture was cooled, poured in water, and extracted with ethylacetate. The organic phase was washed with 20% citric acid, with brine, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed on silica gel using 20% ethylacetate in hexane as eluent to yield 700 gm (37%) of 2-(p-methoxybenzyl)-3-methyl-4-hydroxybenzofuran, mp.130°-133° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethylacetate
  3. washThe organic phase was washed with 20% citric acid, with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel using 20% ethylacetate in hexane as eluent

Sources & evidence

ORD record
ord-0815bb20f2fb4256bb4ceff8fed4dff1
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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