Potassium Carbonate → Methyl 3-(3-methoxypropoxy)-4-methylbenzoate

HRID 1158403ノート

反応式

HRID 1158403 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([OH:11])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH2:21][CH2:22][O:23][CH3:24]>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([O:11][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH:5]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 354091Methyl 3-hydroxy-4-methylbenzoateHCID 135229891-Iodo-3-methoxypropane

生成物 1

HCID 68447108Methyl 3-(3-methoxypropoxy)-4-methylbenzoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 3-hydroxy-4-methyl-benzoic acid methyl ester (7.7 g, 32.43 mmol), potassium carbonate (6.72 g, 48.65 mmol) and 1-iodo-3-methoxy propane (7.14 g, 35.68 mmol) in acetonitrile (125 mL) is stirred at reflux for 26 h. The solvent is concentrated under reduced pressure, H2O (100 mL) is added, and the aqueous layer is extracted with ether (50 mL×4). The combined organic extracts are washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title which is used without further purification in the next step. TLC, Rf (hexane/AcOEt 2:1)=0.65. 1H-NMR (CDCl3, 300 MHz): δ=2.10 (p, 2H), 2.3 (s, 3H), 3.38 (s, 3H), 3.62 (t, 2H), 3.9 (s, 3H), 4.15 (t, 2H), 7.15 (d, 1H), 7.45 (s, 1H), 7.55 (d, 1H) ppm.

後処理

  1. temperatureat reflux for 26 h
  2. concentrationThe solvent is concentrated under reduced pressure, H2O (100 mL)
  3. additionis added
  4. extractionthe aqueous layer is extracted with ether (50 mL×4)
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto afford the title which
  9. customis used without further purification in the next step

出典と根拠

ORDレコード
ord-03540ff7335a4d6c86d1d5ce324524c7
出典データセット
uspto-grants-2010_10
特許番号
US07807709B2

反応ノート

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