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

HRID 1492994Notes

Reaction equation

HRID 1492994 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, 1,0.022 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 NaHCOa 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 NaHCOa 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-b5f7e300399e48d4a3c61c7e6323556f
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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