Methyl iodide → Methyl benzilate

HRID 2121490Notes

Reaction equation

HRID 2121490 reaction equation
[C:1]([OH:17])(=[O:16])[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH2:18]1CCN2C(=NCCC2)CC1.CI>C(#N)C>[CH3:18][O:16][C:1](=[O:17])[C:2]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 6463Benzilic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 66159Methyl benzilate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

90 g (0.394 mol) of benzilic acid are dissolved in 900 mL acetonitrile and at 5° C. 109.6 g (0.72 mol) of DBU are added dropwise. After the addition of 204.4 g (1.44 mol) of methyl iodide, the mixture is stirred for 24 hours at ambient temperature (about 20° C. to 23° C.). The solution is evaporated down to the residue, the residue is taken up in diethyl ether and extracted with water. The organic phase is washed with 5% aqueous sodium carbonate solution and water, dried, and the solvent is distilled off. The product is purified by recrystallization from cyclohexane. Yield: 77.19 g of white crystals (81% of theoretical yield); melting point: 74° C.-76° C.

Workup

  1. customThe solution is evaporated down to the residue
  2. extractionextracted with water
  3. washThe organic phase is washed with 5% aqueous sodium carbonate solution and water
  4. customdried
  5. distillationthe solvent is distilled off
  6. customThe product is purified by recrystallization from cyclohexane

Sources & evidence

ORD record
ord-fe78e8e5e1b84410b8242a8aaf9c63e3
Source dataset
uspto-grants-2004_02
Patent number
US06696462B2

Reaction notes

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