Methyl iodide → HCID 10561438, compound

HRID 1596754Notes

Reaction equation

HRID 1596754 reaction equation
CI.N12CCCN=C1CCCC[CH2:4]2.[O:14]=[C:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([C:27]([OH:29])=[O:28])=[CH:16]1>CC(C)=O>[O:14]=[C:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:17]([C:27]([O:29][CH3:4])=[O:28])=[CH:16]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2956294-Oxo-1,4,5,6-tetrahydro[1,1'-biphenyl]-2-carboxylic acid

Product 1

HCID 10561438HCID 10561438, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

358 g (2.52 mol) of methyl iodide and 361 g (2.38 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene are successively added to a solution of 428 g (1.98 mol) of (RS)-3-oxo-6-phenylcyclohex-1-ene-1-carboxylic acid, which can be obtained according to J. Org. Chem., 1971, 36, 3707, in 4.5 dm3 of acetone and then the reaction mixture is brought to reflux for five hours. The acetone is subsequently distilled off and the residue is stirred with 2.5 dm3 of water. After cooling to 10° C., the precipitate formed is filtered off, washed with ice-cold water and then dried at 30° C. 423 g (93%) of methyl (RS)-3-oxo-6-phenylcyclohex-1-ene-1-carboxylate are thus obtained in the form of a yellow powder, the characteristics of which are as follows:

Workup

  1. customcan be obtained
  2. temperatureto reflux for five hours
  3. distillationThe acetone is subsequently distilled off
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. washwashed with ice-cold water
  7. customdried at 30° C

Sources & evidence

ORD record
ord-b4061364f4ef4935b895b6fd17610d8b
Source dataset
uspto-grants-2001_09
Patent number
US06291679B1

Reaction notes

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