Benzoyl chloride → 3-Benzoyloxy-2-[1-(ethoxyimino)propyl]-5-mesitylcyclohex-2-en-1-one

HRID 846001Notes

Reaction equation

HRID 846001 reaction equation
[OH-].[Na+].[CH2:3]([O:5][N:6]=[C:7]([C:10]1[C:11](=[O:26])[CH2:12][CH:13]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[CH2:14][C:15]=1[OH:16])[CH2:8][CH3:9])[CH3:4].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O.O1CCCC1>[C:27]([O:26][C:11]1[CH2:12][CH:13]([C:17]2[C:18]([CH3:25])=[CH:19][C:20]([CH3:24])=[CH:21][C:22]=2[CH3:23])[CH2:14][C:15](=[O:16])[C:10]=1[C:7](=[N:6][O:5][CH2:3][CH3:4])[CH2:8][CH3:9])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 1354748904-(1-(Ethoxyimino)propyl)-5-hydroxy-2',4',6'-trimethyl-1,6-dihydro-[1,1'-biphenyl]-3(2H)-one

Product 1

HCID 736634413-Benzoyloxy-2-[1-(ethoxyimino)propyl]-5-mesitylcyclohex-2-en-1-oneYield 67.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium hydroxide (0.12 g) in water (0.7 ml) was added dropwise, with stirring, to a solution of 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-en-1-one (0.89 g) in tetrahydrofuran (9.5 ml). Benzoyl chloride (0.42 g) was added dropwise, with stirring and the mixture was stirred at room temperature for a period of 30 minutes. The solvent was removed by evaporation under reduced pressure and the residue was taken up in dichloromethane and water. The dichloromethane solution was separated, washed twice with water, dried, and the solvent evaporated under reduced pressure. The remaining oil was triturated with petroleum ether (b.p. 40°-60° C.) and the solid which formed was recrystallised from isopropanol to give 3-benzoyloxy-2-[1-(ethoxyimino)propyl]-5-mesitylcyclohex-2-en-1-one (0.79 g) as a solid m.p. 94°-95.5° C.

Workup

  1. stirringthe mixture was stirred at room temperature for a period of 30 minutes
  2. customThe solvent was removed by evaporation under reduced pressure
  3. customThe dichloromethane solution was separated
  4. washwashed twice with water
  5. customdried
  6. customthe solvent evaporated under reduced pressure
  7. customThe remaining oil was triturated with petroleum ether (b.p. 40°-60° C.)
  8. customthe solid which formed
  9. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-a9bee19cf39c4e3b9eeec240836d8aae
Source dataset
uspto-grants-1988_07
Patent number
US04760192

Reaction notes

Loading…