Dimethyl Sulfate → Methyl 4-iodo-3-methoxybenzoate

HRID 70286

反応式

HRID 70286 の反応式
O[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6].[C:12](=O)([O-])[O-].[K+].[K+].S([O:23][CH3:24])(OC)(=O)=O>CC(C)=O>[I:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([O:7][CH3:12])=[O:6])=[CH:3][C:2]=1[O:23][CH3:24]

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 7368543-Hydroxy-4-iodobenzoic acid

生成物 1

HCID 11243290Methyl 4-iodo-3-methoxybenzoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 3-hydroxy-4-iodobenzoic acid (3.0 g, 0.011 mol) in acetone (50 mL) was added in one portion potassium carbonate (3.9 g, 0.028 mol). Dimethyl sulfate (3.5 g, 0.028 mol) was added dropwise and the mixture was heated at reflux overnight. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution. The organic phase was washed with brine, dried over sodium sulfated and concentrated in vacuo to give methyl 4-iodo-3-(methyloxy)benzoate as a yellow oil. 1H NMR (DMSO-d6) δ ppm 3.83 (s, 3H, Me), 3.87 (s, 3H, Me), 7.30 (dd, J=8.0, 1.8 Hz, 1H, Ar), 7.40 (d, J=1.7 Hz, 1H, Ar), 7.92 (d, J=8.0 Hz, 1H, Ar).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3fc5470298f94a3ab2e31e37113df2e4
出典データセット
uspto-grants-2014_09
特許番号
US08822518B2

関連ノート

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