Ethanol → Ethyl 2,4-dimethylbenzoate

HRID 1907038노트

반응식

HRID 1907038 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

HCID 118492Ethyl 2,4-dimethylbenzoate수율 95%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2be7d153eea24d71a5c612c88a56299c
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08597631B2

반응 노트

불러오는 중…