Diethyl Malonate → 5-Hydroxy-3'-methoxy-2',4',6'-trimethyl-1,6-dihydro[1,1'-biphenyl]-3(2H)-one

HRID 1382166Notes

Reaction equation

HRID 1382166 reaction equation
C(OCC)(=O)[CH2:2][C:3](OCC)=[O:4].[Na].[CH3:13][O:14][C:15]1[C:16]([CH3:28])=[C:17]([CH:23]=[CH:24][C:25](=[O:27])[CH3:26])[C:18]([CH3:22])=[CH:19][C:20]=1[CH3:21].[OH-].[Na+]>C(O)C>[OH:4][C:3]1[CH2:2][CH:23]([C:17]2[C:18]([CH3:22])=[CH:19][C:20]([CH3:21])=[C:15]([O:14][CH3:13])[C:16]=2[CH3:28])[CH2:24][C:25](=[O:27])[CH:26]=1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 536747854-(3-Methoxy-2,4,6-trimethylphenyl)but-3-en-2-one

Product 1

HCID 138272025-Hydroxy-3'-methoxy-2',4',6'-trimethyl-1,6-dihydro[1,1'-biphenyl]-3(2H)-oneYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl malonate (21.0 g) was added to a solution of sodium metal (3.02 g) in anhydrous absolute ethanol (55 ml) and the mixture was heated to reflux temperature. 1-(3-Methoxy-2,4,6-trimethylphenyl)but-1-en-3-one (27.3 g) was added over a period of 2 minutes and the mixture was heated under reflux for a period of 2 hours. An aqueous solution of sodium hydroxide (16.0 g in 100 ml of water) was added and the mixture was heated under reflux for a further 41/2 hours. The aqueous mixture was cooled and washed with dichloromethane and the aqueous phase was warmed, acidified with dilute aqueous hydrochloric acid and extracted with ethyl acetate. The ethyl acetate phase was washed with water, dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure to give 3-hydroxy-5-(3-methoxy-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (20.5 g) as a colourless crystalline solid, mp 165°-166° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux temperature
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a period of 2 hours
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for a further 41/2 hours
  7. temperatureThe aqueous mixture was cooled
  8. washwashed with dichloromethane
  9. temperaturethe aqueous phase was warmed
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate phase was washed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-a9ef59e046564101a80b50fd8a9cc9e4
Source dataset
uspto-grants-1989_02
Patent number
US04806141

Reaction notes

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