Isobutyryl chloride → HCID 20088786, compound

HRID 275533Notes

Reaction equation

HRID 275533 reaction equation
C([O-])(=O)C.[Na+].C([O:9][C:10]1[C:15]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:14][C:13]([CH:20]([NH:22][OH:23])[CH3:21])=[CH:12][C:11]=1[C:24]([CH3:27])([CH3:26])[CH3:25])(=O)C.[C:28](Cl)(=[O:32])[CH:29]([CH3:31])[CH3:30]>O.O1CCOCC1>[CH3:25][C:24]([C:11]1[CH:12]=[C:13]([CH:20]([N:22]([OH:23])[C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])[CH3:21])[CH:14]=[C:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:10]=1[OH:9])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 62325Isobutyryl chlorideHCID 517045Sodium AcetateHCID 54086794HCID 54086794, compound

Product 1

HCID 20088786HCID 20088786, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.82 g (0.01 mole) of sodium acetate in H2O (7 mL) is added to a solution of 1.07 g (0.0033 mole) of 2,6-bis(1,1-dimethylethyl)-4-[ 1-(hydroxyamino)ethyl]phenol acetate (Example 2) in dioxane (35 mL). Isobutyryl chloride (0.488 g, 0.00458 mole) is added dropwise and the reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is concentrated to half volume, diluted with H2O, and extracted with Et2O. The Et2O extracts are washed with saturated NaHCO3, brine, dried over Na2SO4, and evaporated to dryness. The residue is recrystallized from n-hexane to give white crystals, 0.62 g (56%), m.p. 147°-148.5° C.

Workup

  1. concentrationThe reaction mixture is concentrated to half volume
  2. additiondiluted with H2O
  3. extractionextracted with Et2O
  4. washThe Et2O extracts are washed with saturated NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe residue is recrystallized from n-hexane
  8. customto give white crystals, 0.62 g (56%), m.p. 147°-148.5° C.

Sources & evidence

ORD record
ord-ea11132b086d4801826775f93c8ff2b0
Source dataset
uspto-grants-1995_02
Patent number
US05393923

Reaction notes

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