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

HRID 354535

反応式

HRID 354535 の反応式
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]

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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°).

後処理

  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

出典と根拠

ORDレコード
ord-de9954a06a1e436db4426b380dac932f
出典データセット
uspto-grants-1983_03
特許番号
US04375476

関連ノート

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