Methanol → 2-Methyl-6-phenoxy-benzoic acid

HRID 409224

반응식

HRID 409224 반응식
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO>C[O-].[Na+].[Cu]>[CH3:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:2]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[C:4]([OH:6])=[O:5]

참가 물질

6

반응물 3

HCID 887MethanolHCID 996PhenolHCID 888702-Chloro-6-methylbenzoic acid

생성물 1

HCID 671100872-Methyl-6-phenoxy-benzoic acid수율 66.4%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 10942334Sodium Methoxide용매

실험 절차

2-Chloro-6-methyl-benzoic acid (30 mmol, 5.22 g) and phenol (40 mmol, 3.8 g) were dissolved in a solution of NaOMe (30 wt %) in MeOH (ca. 66 mmol, 12 mL). To the solution was added copper bronze (3 mmol, 193 mg) before it was concentrated in vacuo. Then, 1,2-dichlorobenzene (24 mL) was added and the mixture was refluxed under nitrogen for 2 h with stirring. After cooling to ambient temperature water (200 mL) and Et2O (150 mL) were added and the mixture was stirred vigorously for 30 min before the organic phase was separated and discarded. The aqueous phase was washed with Et2O (150 mL) before it was acidified by addition of 5 N hydrochloric acid. The resulting mixture was extracted with ethyl acetate (1×100 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was recrystallized from hexanes/toluene to give the title compound as a tan solid (4.55 g); MS-(−)-ion: M−1=226.8.

후처리

  1. concentrationwas concentrated in vacuo
  2. additionThen, 1,2-dichlorobenzene (24 mL) was added
  3. temperaturethe mixture was refluxed under nitrogen for 2 h
  4. additionwere added
  5. stirringthe mixture was stirred vigorously for 30 min before the organic phase
  6. customwas separated
  7. washThe aqueous phase was washed with Et2O (150 mL) before it
  8. additionwas acidified by addition of 5 N hydrochloric acid
  9. extractionThe resulting mixture was extracted with ethyl acetate (1×100 mL)
  10. dry with materialThe organic phase was dried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customThe residue was recrystallized from hexanes/toluene

출처 및 근거

ORD 기록
ord-70058d65ba9c4e989e95dd346e67e1e8
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759373B2

연결된 노트

불러오는 중…