Hydrochloric Acid → Ethyl 3-nitro-4-(trifluoromethyl)benzoate

HRID 257575

반응식

HRID 257575 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[C:7]([OH:9])=[O:8])([O-:3])=[O:2].Cl.[CH2:18](O)[CH3:19]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]([F:14])([F:15])[F:16])[C:7]([O:9][CH2:18][CH3:19])=[O:8])([O-:3])=[O:2]

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27790153-Nitro-4-(trifluoromethyl)benzoic acid

생성물 1

HCID 19783148Ethyl 3-nitro-4-(trifluoromethyl)benzoate수율 64%

실험 절차

A solution of 555 mg (2.36 mmol) of 3-nitro-4-(trifluoromethyl)benzoic acid (from Step B) in 10 mL of ethanol was treated with 1 mL of concentrated hydrochloric acid. The solution was stirred at reflux for 2 days, then cooled, and partitioned between ethyl acetate and H2O. The organic layer was washed successively with saturated NaHCO3, H2O, and brine. The ethyl acetate solution was then dried over Na2SO4 and concentrated to give 400 mg (64%) of the title compound as a pale yellow foam, homogeneous by TLC in 4:1 hexane-EtOAc; mass spectrum (EI) m/e 263 (M+). 200 MHz 1H NMR (CDCl3) δ1.43 (t, J=7.2 Hz, 3H), 4.46 (q, J=7.2 Hz, 2H), 7.92 (d, J=8 Hz, 1H), 8.36 (d, J=8 Hz, 1H), 8.49 (s, 1H).

후처리

  1. temperatureat reflux for 2 days
  2. temperaturecooled
  3. custompartitioned between ethyl acetate and H2O
  4. washThe organic layer was washed successively with saturated NaHCO3, H2O, and brine
  5. dry with materialThe ethyl acetate solution was then dried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3405e901a97141a080d0db29b9748383
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262412

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