Methanol → 12-Methoxydodecanoate

HRID 1461007

反応式

HRID 1461007 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[OH-:16].[K+].[CH3:18]O>>[CH3:18][O:16][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

参加物

4

反応物 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 17546812-Bromododecanoic Acid

生成物 1

HCID 142012-Methoxydodecanoate収率 39%

実験手順

12-bromododecanoic acid (2.0 g, 7.16 mmol) was added to a solution of potassium hydroxide (1.61 g, 28.65 mmol) in methanol (30 mLs) and refluxed for 20 hrs. After cooling and acidification with HCl, solvent was removed under reduced pressure. The sample was dissolved in ethyl acetate and extracted with water. The organic phase was dried over sodium sulfate, and the solvent removed under reduced pressure. The product was purified by silica column chromatography in 1% diethyl ether/0.3% formic acid/methylene chloride to yield 12-(methoxy)dodecanoic acid (640 mg, 39%): mp 45-47° C.; 1H NMR (300 MHz, CDC13) δ 1.20-1.45 (bm, 15H, methylene envelope), 1.51-1.69 (bm, 4H, 0-CH2 --CH2, CH2 --CH2 --COOH), 2.34 (t, 2H, J=7.4, CH2 --COOH), 3.34 (s, 3H, 0-CH3), 3.38 (t, 2H, J=6.7, 0--CH2), 10.99 (br, 1H, COOH); 13C NMR (75.4 MHz, CDC13) δ 24.75 26.16, 29.10, 29.27, 29.38, 29.44, 29.53, 34.12, 58.50, 72.97, 179.70; m/z 231 (M+H+).

後処理

  1. temperaturerefluxed for 20 hrs
  2. temperatureAfter cooling
  3. customacidification with HCl, solvent was removed under reduced pressure
  4. dissolutionThe sample was dissolved in ethyl acetate
  5. extractionextracted with water
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customthe solvent removed under reduced pressure
  8. customThe product was purified by silica column chromatography in 1% diethyl ether/0.3% formic acid/methylene chloride

出典と根拠

ORDレコード
ord-617dcfe2d9654053ac3fb0029be0890a
出典データセット
uspto-grants-1991_12
特許番号
US05073571

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