Hydrochloric Acid → HCID 178423842, compound

HRID 501810Notes

Reaction equation

HRID 501810 reaction equation
Br[CH:2]([CH:8](Br)[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:3](OCC)=[O:4].Cl.[NH2:18][OH:19].C[O-].[Na+].Cl>CO.C(OCC)(=O)C.O>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]2[O:19][N:18]=[C:3]([OH:4])[CH:2]=2)=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 12765432HCID 12765432, compound

Product 1

HCID 178423842HCID 178423842, compoundYield 68.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.35 g of ethyl 2,3-dibromo-3-(4-methylphenyl)propanoate and 0.083 g of hydroxylamine hydrochloride was suspended in 7 mL of methanol, to which 0.19 g of a 28% solution of sodium methoxide in methanol was added at room temperature, and then this solution was stirred for 12 hours at the same temperature. The reaction mixture, to which water was added, was adjusted to pH 1 with 6M hydrochloric acid followed by addition of ethyl acetate, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out therefrom under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=4:1] to yield 0.12 g of 5-(4-methylphenyl)-3-isoxazolol as yellow oil.

Workup

  1. additionwas added at room temperature
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out therefrom under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-21bd6d8a378f4cff8134adbe00a70c00
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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