Ethylene Glycol → Ethyl 2-(2-methyl-1,3-dioxolan-2-yl)butanoate

HRID 1024345

反応式

HRID 1024345 の反応式
[CH3:1][O:2][C:3](=[O:10])[CH:4]([CH2:8][CH3:9])[C:5]([CH3:7])=[O:6].[CH2:11]([OH:14])[CH2:12]O.[CH3:15]C1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([O:2][C:3](=[O:10])[CH:4]([C:5]1([CH3:7])[O:14][CH2:11][CH2:12][O:6]1)[CH2:8][CH3:9])[CH3:15]

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 103534Butanoic acid, 2-ethyl-3-oxo-, methyl esterHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 12948748Ethyl 2-(2-methyl-1,3-dioxolan-2-yl)butanoate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Methyl-2-ethylacetoacetate (100 mL) was taken up in toluene (250 mL). Ethylene glycol (46.9 mL, 1.35 equiv.) and a catalytic amount of p-TsOH.H2O were added, and the mixture was refluxed overnight under Dean-Stark conditions. After cooling to ambient temperature, the mixture was washed with 5% aqueous NaHCO3 and saturated aqueous NaCl, the organic phase was dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by repeated vacuum distillation (118-128° C., 15 mbar), yielding 85.5 g of product. 1H NMR (400 MHz, CDCl3) δ 0.90 (t, J=7 Hz, 3H), 1.28 (t, J=7 Hz, 3H), 1.40 (s, 3H), 1.59-1.83 (m, 2H), 2.56 (dd, J=11.5 and 4 Hz, 1H), 3.90-4.06 (m, 4H), 4.18 (m, 2H).

後処理

  1. temperaturethe mixture was refluxed overnight under Dean-Stark conditions
  2. washthe mixture was washed with 5% aqueous NaHCO3 and saturated aqueous NaCl
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customevaporated under reduced pressure
  5. distillationThe residue was purified by repeated vacuum distillation (118-128° C., 15 mbar)

出典と根拠

ORDレコード
ord-3524af23d3594868b08969d5f4ba1113
出典データセット
uspto-grants-2014_05
特許番号
US08722887B2

関連ノート

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