Ethanol → Ethyl 4-cyanobenzoate

HRID 563213

反応式

HRID 563213 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH2:17][CH3:18])=[O:8])=[CH:5][CH:4]=1)#[N:2]

参加物

4

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 120874-Cyanobenzoic acid

生成物 1

HCID 81589Ethyl 4-cyanobenzoate収率 73%

実験手順

To a 250 mL round bottom flask charged with 4-cyanobenzoic acid (19.36 g, 0.13 mol) in abs. ethanol (100 mL) was added concentrated sulfuric acid (3 mL). This mixture was heated to reflux for a period of 28 h, then allowed to cool to room temperature overnight. The solvent was removed via rotary evaporation and the resulting off-white residue was taken up in diethyl ether (500 mL). This was then washed with saturated sodium bicarbonate/water solution (5×100 mL), then brine (1×100 mL), and dried over magnesium sulfate. Filtration and concentration yielded an off-white solid. Recrystallization from 95% ethanol (50 mL) yielded product as white crystals (16.85 g, 73%). 1H NMR (400 MHz, CDCl3, δ in ppm) 8.14 (AA′XX′, J=8.6 Hz, 2H), 7.74 (AA′XX′, J=8.6 Hz, 2H), 4.42 (q, J=7.1 Hz, 2H), 1.41 (t, J=7.1 Hz, 3H).

後処理

  1. temperatureThis mixture was heated
  2. temperatureto reflux for a period of 28 h
  3. customThe solvent was removed via rotary evaporation
  4. washThis was then washed with saturated sodium bicarbonate/water solution (5×100 mL)
  5. dry with materialbrine (1×100 mL), and dried over magnesium sulfate
  6. filtrationFiltration and concentration
  7. customyielded an off-white solid
  8. customRecrystallization from 95% ethanol (50 mL)

出典と根拠

ORDレコード
ord-8de66ee243544cf890120de0db2f221c
出典データセット
uspto-grants-2011_11
特許番号
US08067448B2

関連ノート

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