Dimethylformamide → Dimethyl 3-ethyl-5-methoxyphthalate

HRID 1360326Notes

Reaction equation

HRID 1360326 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].CI.[CH2:9]([C:11]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:13]([C:14]([OH:16])=[O:15])[C:12]=1[C:22]([OH:24])=O)[CH3:10].CN([CH:28]=[O:29])C>>[CH2:9]([C:11]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:13]([C:14]([O:16][CH3:1])=[O:15])[C:12]=1[C:22]([O:29][CH3:28])=[O:24])[CH3:10]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide3×HCID 11430Potassium CarbonateHCID 66969973HCID 66969973, compound

Product 1

HCID 20139164Dimethyl 3-ethyl-5-methoxyphthalate

Procedure

K2CO3 (63.9 g, 462 mmol) and MeI (28.8 mL, 462 mmol) were added to a solution of compound H (34.6 g, 154 mmol) in DMF (500 mL) at 0° C. The mixture was warmed to room temperature and stirred for 2 h, and at 40° C. for 1 h. MeI (28.8 mL, 462 mmol) was added and the mixture was stirred for 14 h. Additional MeI (28.8 mL, 462 mmol) was then added to the reaction mixture. After being stirred for 8 h, the mixture was concentrated in vacuo and water was added to the residue. The aqueous phase was extracted 3 times with ethyl acetate and the combined organic phases were washed with H2O, then brine, and dried over Na2SO4. The organic phase was then concentrated in vacuo and purified by silica gel column chromatography (ethyl acetate:hexane=1:6), yielding the desired compound I (36.0 g, 143 mmol) as a pale-yellow oil.

Workup

  1. waitat 40° C. for 1 h
  2. stirringthe mixture was stirred for 14 h
  3. stirringAfter being stirred for 8 h
  4. concentrationthe mixture was concentrated in vacuo and water
  5. additionwas added to the residue
  6. extractionThe aqueous phase was extracted 3 times with ethyl acetate
  7. washthe combined organic phases were washed with H2O
  8. dry with materialbrine, and dried over Na2SO4
  9. concentrationThe organic phase was then concentrated in vacuo
  10. custompurified by silica gel column chromatography (ethyl acetate:hexane=1:6)

Sources & evidence

ORD record
ord-e23893d59acc4596aa89a6b831bb1cea
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

Loading…