Sodium Hydroxide → 4-(1-(Ethoxyimino)propyl)-5-hydroxy-2',4',6'-trimethyl-1,6-dihydro-[1,1'-biphenyl]-3(2H)-one

HRID 845999Notes

Reaction equation

HRID 845999 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])=[CH:17][C:16]=2[CH3:23])[CH2:12][C:11](=[O:24])[C:10]=1[C:25](=O)[CH2:26][CH3:27]>C(O)C>[CH2:2]([O:4][N:5]=[C:25]([C:10]1[C:9](=[O:8])[CH2:14][CH:13]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[CH2:12][C:11]=1[OH:24])[CH2:26][CH3:27])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 178458835HCID 178458835, compound

Product 1

HCID 1354748904-(1-(Ethoxyimino)propyl)-5-hydroxy-2',4',6'-trimethyl-1,6-dihydro-[1,1'-biphenyl]-3(2H)-oneYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethoxyamine hydrochloride (0.45 g) and then aqueous 1% sodium hydroxide (18.4 ml) were added to a solution of 3-hydroxy-5-mesityl-2-propionylcyclohex-2-en-1-one (1.2 g; 4.2 mmole) 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 using a rotary evaporator. 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 the product, 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-en-1-one (1.25 g; 93%), as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-7212b36df20b47f3a32e637558edb7d7
Source dataset
uspto-grants-1988_07
Patent number
US04760192

Reaction notes

Loading…