Ethanol → Benzoic acid, 3-fluoro-4-methyl-, ethyl ester

HRID 371527노트

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HRID 371527 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH3:17][CH2:18]O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH2:17][CH3:18])=[O:6]

참가 물질

5

반응물 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 676873-Fluoro-p-toluic acid

생성물 1

HCID 13489923Benzoic acid, 3-fluoro-4-methyl-, ethyl ester수율 92%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 10.2 g (66.2 mmol) of 3-fluoro-4-methylbenzoic acid in 50 mL of EtOH and 25 mL of toluene containing 0.2 mL of H2SO4 was heated gradually to 120° C. (oil bath temperature), and the solvent was removed by distillation over a period of 2.25 h through a 10-cm Vigreux column. The residue was cooled, treated with a further 50 mL of EtOH and 25 mL of toluene, and the distillation was repeated. The residual solution, containing some white solid, was poured into 75 mL of aqueous NaHCO3 and extracted with hexane (75 mL, then 50 mL). The extract was washed with water (2×75 mL), dried (Na2SO4), and concentrated. The pale-yellow liquid was distilled, bp 49°-58° C. (0.01-0.05 mm) to give 11.1 g (92% yield) of ethyl 3-fluoro-4-methylbenzoate as a colorless liquid: IR (CHCl3) 1720 (C=O), 1580, 1420, 1370, 1290, 1190, 1130, 1090, 1020, 940, 895 cm-1 ; 1H NMR (CDCl3) δ 1.40 (t, J=7 Hz, 3, CO2CH2CH3), 2.32 (d, J=2 Hz, 3, ArCH3), 4.37 (q, J=7 Hz, 2, CO2CH2CH3), 7.22 (dd, J=8 Hz, J=8 Hz, 1, 6' H), 7.68 (m, 2, 3', 5' H); MS calcd for C10H11FO2 182.0743, found 182.0729.

후처리

  1. customthe solvent was removed by distillation over a period of 2.25 h through a 10-cm Vigreux column
  2. temperatureThe residue was cooled
  3. additiontreated with a further 50 mL of EtOH and 25 mL of toluene
  4. distillationthe distillation
  5. additionThe residual solution, containing some white solid
  6. additionwas poured into 75 mL of aqueous NaHCO3
  7. extractionextracted with hexane (75 mL
  8. washThe extract was washed with water (2×75 mL)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. distillationThe pale-yellow liquid was distilled

출처 및 근거

ORD 기록
ord-bea8b58487454669b193521754901c15
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04532343

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