Water → HCID 14579771, compound

HRID 1607259Notes

Reaction equation

HRID 1607259 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[O:10][C:11]3[C:18]([CH2:19][CH2:20][CH3:21])=[CH:17][C:16]([CH2:22][CH2:23][CH3:24])=[C:15]([OH:25])[C:12]=3[C:13]=2[CH3:14])=O)=[CH:5][CH:4]=1.NN.[OH-].[K+].O>C(O)CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:9]2[O:10][C:11]3[C:18]([CH2:19][CH2:20][CH3:21])=[CH:17][C:16]([CH2:22][CH2:23][CH3:24])=[C:15]([OH:25])[C:12]=3[C:13]=2[CH3:14])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 14579770HCID 14579770, compound

Product 1

HCID 14579771HCID 14579771, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of 2 (p-methoxybenzoyl)-3 methyl-4-hydroxy-5,7-dipropylbenzofuran (0.30 gm; 0.80 mmoles), 99% hydrazine (0.2 mL), potassium hydroxide (0.40 gm; 7mmoles) in ethylene glycol (10 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 into 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 140 mg (50%) of 2-(p-methoxybenzyl)-3-methyl-4-hydroxy-5,7-dipropylbenzofuran, mp. 70°-72° 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-b19ca7912bb54909a96ca6826ac0295d
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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