Methyl iodide → HCID 10561438, compound

HRID 849593Notes

Reaction equation

HRID 849593 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 were successively added to a solution of 428 g (1.98 mol) of (RS)-3-oxo-6-phenylcyclohex-1-ene-1-carboxylic acid, which was obtained according to J. Org. Chem., 1971, 36, 3707, in 4.5 cm3 of acetone and then the reaction mixture was brought to reflux for five hours. The acetone was subsequently distilled off and then the residue was stirred with 2.5 dm3 of water. After cooling to 10° C., the precipitate formed was 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 were thus obtained in the form of a yellow powder, the characteristics of which were as follows:

Workup

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

Sources & evidence

ORD record
ord-5ef0852ca72848c3b91dd8699f249816
Source dataset
uspto-grants-2000_01
Patent number
US06013662

Reaction notes

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