Methyl iodide → methyl (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylate

HRID 324674Notes

Reaction equation

HRID 324674 reaction equation
CI.N12CCCN=C1CCCC[CH2:4]2.[CH3:14][C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[C:16]1[C:22]([OH:24])=[O:23]>CC(C)=O>[CH3:14][C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[C:16]1[C:22]([O:24][CH3:4])=[O:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20647081(RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylic acid

Product 1

HCID 20647083methyl (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylateYield 94.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.88 cm3 (14 mmol) of methyl iodide and 1.8 cm3 (12 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, dropwise, were successively added to a solution of 2.3 g (10 mmol) of (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylic acid in 20 cm3 of acetone. The reaction mixture was subsequently heated at reflux for two hours. The acetone was subsequently concentrated, the residue was then stirred with 100 cm3 of water and then extracted with three times 30 cm3 of ethyl acetate. After drying over magnesium sulphate and concentrating under reduced pressure, 2.3 g (94%) of methyl (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylate were obtained in the form of an orange oil, the characteristic of which was as follows:

Workup

  1. temperatureThe reaction mixture was subsequently heated
  2. temperatureat reflux for two hours
  3. concentrationThe acetone was subsequently concentrated
  4. extractionextracted with three times 30 cm3 of ethyl acetate
  5. dry with materialAfter drying over magnesium sulphate
  6. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-0878c66fd24c4821951962bf9ef5557f
Source dataset
uspto-grants-2001_04
Patent number
US06218406B1

Reaction notes

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