Methyl iodide → Methyl benzilate

HRID 33418

Reaction equation

HRID 33418 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>[C:1]([O:17][CH3:18])(=[O:16])[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

Conditions

Temperature
21.5 °C

Procedure

90 g (0.394 mol) 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 20-23° 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 recrystallisation from cyclohexane. Yield: 77.19 g white crystals (=81% of theory) Melting point: 74°-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 recrystallisation from cyclohexane

Sources & evidence

ORD record
ord-bec04017e03645b4b20b9f5bb286aff1
Source dataset
uspto-grants-2008_09
Patent number
US07429601B2

Linked notes

Loading…