Hydrochloric Acid → 3,5-Bis(1,1-dimethylethyl)-4-hydroxycinnamic acid hydrazide

HRID 466048Notes

Reaction equation

HRID 466048 reaction equation
CC([N:5](C(O)=O)[NH:6][C:7](=[O:25])[CH:8]=[CH:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=1)(C)C.Cl>C(O)C>[CH3:19][C:16]([C:14]1[CH:15]=[C:10]([CH:11]=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:13]=1[OH:20])[CH:9]=[CH:8][C:7]([NH:6][NH2:5])=[O:25])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 543996901,1-Dimethylethyl 2-[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxo-2-propenyl]hydrazinecarboxylic acid

Product 1

HCID 730977023,5-Bis(1,1-dimethylethyl)-4-hydroxycinnamic acid hydrazideYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,1-Dimethylethyl 2-[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxo-2-propenyl]hydrazinecarboxylic acid (4.3 g, 0.011 mole) in absolute ethanol (20 ml) is treated with aqueous 2M HCl (11.0 ml, 0.022 mole). The resulting mixture is heated on a steam-bath for one hour. The mixture is stripped of volatiles under reduced pressure and the residue partitioned between ether and water. The layers are separated and the aqueous phase is treated with saturated aqueous NaHCO3 until basic. The product is extracted out with a mixture of 1:1 ethyl acetate/ether. The organic extract is washed with saturated aqueous NaCl and dried over MgSO4. Filtration and concentration provides a solid which is triturated in hot hexane and filtered to yield 3.0 g (3.2 g theor., 94%) of 3,5-bis(1,1-dimethylethyl)-4-hydroxycinnamic acid hydrazide, mp 166° C.

Workup

  1. temperatureThe resulting mixture is heated on a steam-bath for one hour
  2. customthe residue partitioned between ether and water
  3. customThe layers are separated
  4. additionthe aqueous phase is treated with saturated aqueous NaHCO3 until basic
  5. extractionThe product is extracted out with a mixture of 1:1 ethyl acetate/ether
  6. extractionThe organic extract
  7. washis washed with saturated aqueous NaCl
  8. dry with materialdried over MgSO4
  9. filtrationFiltration and concentration
  10. customprovides a solid which
  11. customis triturated in hot hexane
  12. filtrationfiltered

Sources & evidence

ORD record
ord-deabc5963c9d44f7b5c335829612712e
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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