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

HRID 1657062ノート

反応式

HRID 1657062 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4135517e256c4b6693f59f0d5b14b3f7
出典データセット
uspto-grants-1993_10
特許番号
US05256680

反応ノート

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