Methanol → (2,6-Dimethyl-3-nitrophenyl)methanol

HRID 354535

반응식

HRID 354535 반응식
CC1C=CC=C(C)C=1C(O)=O.[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([CH3:25])[C:14]=1[C:15]([OH:17])=[O:16].CO>O1CCCC1>[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([CH3:25])[C:14]=1[C:15]([OH:17])=[O:16].[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([CH3:25])[C:14]=1[CH2:15][OH:16]

참가 물질

6

반응물 3

HCID 887MethanolHCID 124392,6-Dimethylbenzoic acidHCID 2393292,6-Dimethyl-3-nitrobenzoic acid

생성물 2

HCID 2393292,6-Dimethyl-3-nitrobenzoic acidHCID 10487641(2,6-Dimethyl-3-nitrophenyl)methanol수율 88.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2,6-Dimethyl-3-nitrobenzoic acid was prepared by nitrating 2,6-dimethylbenzoic acid. A solution of 2,6-dimethyl-3-nitrobenzoic acid (30 grams, 0.15 mole) in tetrahydrofuran (100 ml) was stirred under nitrogen. Borane-methyl sulfide complex (20 ml, 0.2 mole) was added dropwise at room temperature. When one fourth of the borane complex had been added the reaction mixture was brought to reflux. Reflux continued for one hour after complete addition of the borane complex. The reaction mixture was cooled to 0°, and cold methanol (500 ml) was added dropwise until foaming ceased and then added rapidly. The solvent was evaporated, and the crude product was dissolved in methylene chloride and washed with 2 N sodium hydroxide. The solvent was removed by evaporation to give (2,6-dimethyl-3-nitrophenyl)methanol (12.0 grams; mp 84°-92°).

후처리

  1. additionBorane-methyl sulfide complex (20 ml, 0.2 mole) was added dropwise at room temperature
  2. additionWhen one fourth of the borane complex had been added the reaction mixture
  3. temperatureto reflux
  4. temperatureReflux
  5. additionafter complete addition of the borane complex
  6. temperatureThe reaction mixture was cooled to 0°
  7. additionadded rapidly
  8. customThe solvent was evaporated
  9. dissolutionthe crude product was dissolved in methylene chloride
  10. washwashed with 2 N sodium hydroxide
  11. customThe solvent was removed by evaporation

출처 및 근거

ORD 기록
ord-de9954a06a1e436db4426b380dac932f
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04375476

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