Methyl iodide → Methyl 2,2-diphenylpropionate

HRID 2099336Notes

Reaction equation

HRID 2099336 reaction equation
[CH2:1]1CCN2C(=NCCC2)CC1.[C:12]1([C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH3:22])[C:19]([OH:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CI>C(#N)C>[C:12]1([C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH3:22])[C:19]([O:21][CH3:1])=[O:20])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 796762,2-Diphenylpropionic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 15259765Methyl 2,2-diphenylpropionate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

37.60 g (0.247 mol) of DBU are added dropwise to a suspension of 50.8 g (0.225 mol) of 2,2-diphenylpropionic acid and 200 mL of acetonitrile at 20° C. 70.10 g (0.494 mol) of methyl iodide are added dropwise to the resulting solution within 30 minutes. Then the mixture is stirred overnight at 20° C. The solvent is evaporated down, the residue is extracted with diethylether/water, the organic phase is washed with water, dried over Na2SO4, and evaporated to dryness. Yield: 48.29 g of viscous residue 3.1. (89% of theory).

Workup

  1. customThe solvent is evaporated down
  2. extractionthe residue is extracted with diethylether/water
  3. washthe organic phase is washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-ac68ede47bde44fa9e9566ae22c57e64
Source dataset
uspto-grants-2009_08
Patent number
US07569581B2

Reaction notes

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