Ethanol → Ethyl 2,4-dimethylbenzoate

HRID 1907038ノート

反応式

HRID 1907038 の反応式
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[OH-].[Ca+2].[OH-].[CH2:20](O)[CH3:21]>>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:20][CH3:21])=[O:5]

参加物

5

反応物 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 118972,4-Dimethylbenzoic acidHCID 6093208Calcium Hydroxide

生成物 1

HCID 118492Ethyl 2,4-dimethylbenzoate収率 95%

実験手順

To a solution of commercially available 2,4-dimethylbenzoic acid (67.8 g, 451 mmol) in 1000 mL of ethanol was added 10 mL of sulfuric acid. The mixture was refluxed over night, cooled down and was neutralized by adding calcium hydroxide in small portions (˜30 g). The suspension was filtered over celite and concentrated in vacuo. The crude product was purified by vacuum distillation yielding 76.4 g (95%) of 1 as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 1.38 (t, J=7.3 Hz, 3H), 2.34 (s, 3H), 2.57 (s, 3H), 4.33 (q, J=7.2 Hz, 2H), 7.01-7.06 (m, 2H), 7.82 (d, J=8.5 Hz, 1H); 13C-NMR (100 MHz, CDCl3): δ 14.3, 21.3, 21.7, 60.4, 126.3, 126.9, 130.7, 132.4, 140.1, 142.3, 167.6; MS (ESI) m/z=133.0 (100), 132.0 (57), 178.1 (M+, 51).

後処理

  1. temperatureThe mixture was refluxed over night
  2. temperaturecooled down
  3. filtrationThe suspension was filtered over celite and
  4. concentrationconcentrated in vacuo
  5. distillationThe crude product was purified by vacuum distillation

出典と根拠

ORDレコード
ord-2be7d153eea24d71a5c612c88a56299c
出典データセット
uspto-grants-2013_12
特許番号
US08597631B2

反応ノート

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