Ethanol → HCID 86750438, compound

HRID 975239Notes

Reaction equation

HRID 975239 reaction equation
[CH3:1][CH:2]([CH3:13])[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:5]=O.[Cl-].[OH:15][NH3+:16].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][CH:2]([CH3:13])[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:5]=[N:16][OH:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 21645Hydroxylamine HClHCID 5401244-Methyl-2-phenyl-2-pentenal

Product 1

HCID 86750438HCID 86750438, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-methyl-2-phenyl-2-pentenal (5.0 g, 29 mmol) and hydroxylammonium chloride (2.5 g, 36 mmol) in a mixture of absolute ethanol (15 ml) and water (5 ml) was carefully added a solution of sodium carbonate (7.3 g, 69 mmol) in water (20 ml). After stirring for 5 h a precipitate was filtered off and dried in the air. The crude product was purified by column chromatography on silica gel (50 g, cyclohexane/ethyl acetate 3/1) to give 3.2 g of 4-methyl-2-phenyl-2-pentenal oxime as a solid. M.p. 107°-110° C.

Workup

  1. filtrationwas filtered off
  2. customdried in the air
  3. customThe crude product was purified by column chromatography on silica gel (50 g, cyclohexane/ethyl acetate 3/1)

Sources & evidence

ORD record
ord-6f3da2412bfa4e809937a744db07dd90
Source dataset
uspto-grants-1997_03
Patent number
US05608069

Reaction notes

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