3-(Trifluoromethyl)anisole → 2-Methoxy-6-(trifluoromethyl)benzoic acid

HRID 477270

반응식

HRID 477270 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.[C:18](=[O:20])=[O:19].CCOCC>O1CCCC1.O>[CH3:10][O:9][C:5]1[C:4]([C:18]([OH:20])=[O:19])=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:8]=[CH:7][CH:6]=1

참가 물질

6

반응물 3

HCID 966913-(Trifluoromethyl)anisoleHCID 86742199Dry ice diethyl etherHCID 178418339Butyllithium

생성물 1

HCID 150175332-Methoxy-6-(trifluoromethyl)benzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-trifluoromethylanisol (50.0 g, 0.28 mole) in tetrahydrofuran was cooled to -78° C. under nitrogen atmosphere with stirring. To this solution was added n-butyl lithium (114 ml of 2.5M, 0.28 mole), dropwise at such a rate that the temperature did not exceed -65° C. When the addition was complete, the mixture was stirred at -78° l C. for three hours. The mixture was then poured over a slurry of dry ice/ether and allowed to come to room temperature. The solvent was removed under reduced pressure to give a white solid. This solid was dissolved in a minimum amount of water, extracted with diethyl ether (2×100 ml) and the aqueous phase was acidified to pH 2 with dilute hydrochloric acid. An oil formed and was extracted with diethyl ether, washed several times with water and dried over magnesium sulfate. The solvent was removed to give 45.6 g (74 percent of theory) of the title compound as a white solid of m.p. 129°- 130° C.

후처리

  1. customdid not exceed -65° C
  2. additionWhen the addition
  3. stirringthe mixture was stirred at -78° l C
  4. customto come to room temperature
  5. customThe solvent was removed under reduced pressure
  6. customto give a white solid
  7. extractionextracted with diethyl ether (2×100 ml)
  8. customAn oil formed
  9. extractionwas extracted with diethyl ether
  10. washwashed several times with water
  11. dry with materialdried over magnesium sulfate
  12. customThe solvent was removed

출처 및 근거

ORD 기록
ord-8c0649a8953a4a4f947697013be77b79
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886883

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