Hydroxylamine, O-(3-chloro-2-propenyl)-, hydrochloride → 2-[1-(3-Chloroallyloxyimino)propyl]-3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one

HRID 1906351Notes

Reaction equation

HRID 1906351 reaction equation
Cl.[Cl:2][CH:3]=[CH:4][CH2:5][O:6][NH2:7].C([O-])(=O)C.[Na+].[OH:13][C:14]1[CH2:19][CH:18]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([C:28](=[O:32])/[CH:29]=[CH:30]/[CH3:31])[C:21]=2[CH3:33])[CH2:17][C:16](=[O:34])[C:15]=1[C:35](=O)[CH2:36][CH3:37]>C(O)C>[Cl:2][CH:3]=[CH:4][CH2:5][O:6][N:7]=[C:35]([C:15]1[C:14](=[O:13])[CH2:19][CH:18]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([C:28](=[O:32])/[CH:29]=[CH:30]/[CH3:31])[C:21]=2[CH3:33])[CH2:17][C:16]=1[OH:34])[CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 158057Hydroxylamine, O-(3-chloro-2-propenyl)-, hydrochlorideHCID 517045Sodium AcetateHCID 178450140HCID 178450140, compound

Product 1

HCID 1363321822-[1-(3-Chloroallyloxyimino)propyl]-3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-oneYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloroallyloxyamine hydrochloride (0.3 g) and then anhydrous sodium acetate (0.2 g) were added to a solution of 3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one (0.7 g) in anhydrous ethanol (80 ml). The mixture was stirred briefly then allowed to stand at room temperature for 16 hours. The ethanol was removed by evaporation under reduced pressure using a rotary evaporator. The residue was treated with chloroform and the organic phase was washed twice with water (50 ml). The chloroform layer was dried over magnesium sulphate and the solvent was removed by evaporation under reduced pressure to give the product 2-[1-(3-chloroallyloxyimino)propyl]-3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.7 g, 85%) as a colourless oil. Proton magnetic spectrum (CDCl3 ; δ in ppm); 1.19 (3H, t); 1.92 (3H, d, J=7 Hz); 2.09 (3H, s); 2.19 (3H, s); 2.39 (3H, s); 2.2-4.0 (7H, m); 4.4-4.8 (2H, m); 5.86.7 (4H, m); 6.86 (1H, s); 15.2 (1 H, bs).

Workup

  1. customThe ethanol was removed by evaporation under reduced pressure
  2. customa rotary evaporator
  3. additionThe residue was treated with chloroform
  4. washthe organic phase was washed twice with water (50 ml)
  5. dry with materialThe chloroform layer was dried over magnesium sulphate
  6. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4d235abf22ff4279bf3c3715ecec8224
Source dataset
uspto-grants-1987_03
Patent number
US04652303

Reaction notes

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