Sodium Hydroxide → 2-[1-(Ethoxyimino)propyl]-3-hydroxy-5-(3-methoxy-2,4,6-trimethylphenyl)cyclohex-2-en-1-one

HRID 1382168Notes

Reaction equation

HRID 1382168 reaction equation
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].[OH-].[Na+].[OH:8][C:9]1[CH2:14][CH:13]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]([O:23][CH3:24])[C:16]=2[CH3:25])[CH2:12][C:11](=[O:26])[C:10]=1[C:27](=O)[CH2:28][CH3:29]>C(O)C>[CH2:2]([O:4][N:5]=[C:27]([C:10]1[C:11](=[O:26])[CH2:12][CH:13]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]([O:23][CH3:24])[C:16]=2[CH3:25])[CH2:14][C:9]=1[OH:8])[CH2:28][CH3:29])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 178458847HCID 178458847, compound

Product 1

HCID 1359992872-[1-(Ethoxyimino)propyl]-3-hydroxy-5-(3-methoxy-2,4,6-trimethylphenyl)cyclohex-2-en-1-oneYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethoxyamine hydrochloride (0.43 g) and then aqueous sodium hydroxide (0.18 g in 10.0 ml of water) were added to a solution of 3-hydroxy-5-(3-methoxy-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one (1.35 g) in anhydrous absolute ethanol (200 ml). The mixture was stirred at room temperature for a period of 4 hours and then the ethanol was removed by evaporation under reduced pressure. The residue was treated with dichloromethane and the organic phase was washed twice with dilute aqueous hydrochloric acid and twice with water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure to give 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(3-methoxy-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (1.40 g), as a pale yellow oil which slowly solidified on standing. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.20 (3H, t); 1.32 (3H, t); 2.23 (3H, s); 2.34 (6H, s); 2.35-4.00 (7H, m); 3.65 (3H, s); 4.12 (2H, q); 6.83 (1H, s); 14.95 (1H, s).

Workup

  1. customthe ethanol was removed by evaporation under reduced pressure
  2. additionThe residue was treated with dichloromethane
  3. washthe organic phase was washed twice with dilute aqueous hydrochloric acid and twice with water
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d962d66b9fef490b92d7e05b84f6296c
Source dataset
uspto-grants-1989_02
Patent number
US04806141

Reaction notes

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