Hydrazine hydrate (1:1) → 3-(4-Hydroxy-3-methylbenzofuran-2-yl)propionic acid

HRID 978120Notes

Reaction equation

HRID 978120 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH3:16])=[C:9](/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.O.NN>O.S([O-])([O-])(=O)=O.[Cu+2].CO>[OH:1][C:2]1[C:7]2[C:8]([CH3:16])=[C:9]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13849550E-3-(4-hydroxy-3-methylbenzofuran-2-yl)propenoic acid

Product 1

HCID 138495513-(4-Hydroxy-3-methylbenzofuran-2-yl)propionic acidYield 21.6%

Reagents, catalysts & solvents 2

HCID 61499Cupric sulfate monohydrateCatalystHCID 887MethanolSolvent

Procedure

A mixture of E-3-(4-hydroxy-3-methylbenzofuran-2-yl)propenoic acid (4.5 g, 20 mmoles), methanol (250 ml), 99% hydrazine hydrate (5 ml) and copper sulfate monohydrate (3 crystals) was stirred at room temperature for several days. The mixture was filtered and concentrated to remove methanol. The aqueous residue was acidified with 20% citric acid solution and extracted with diethyl ether. The ether solution was dried with Na2SO4, filtered, concentrated and chromatographed to obtain 950 mg of the title compound, m.p. 114°-117° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customto remove methanol
  4. extractionextracted with diethyl ether
  5. dry with materialThe ether solution was dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed

Sources & evidence

ORD record
ord-66a8950cc8004c1da350a0eed19877a3
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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