6-Methyl-2-nitrobenzoic acid → (2-Methyl-6-nitrophenyl)methanol

HRID 1589932ノート

反応式

HRID 1589932 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4](O)=[O:5].B.C1COCC1>O1CCCC1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[CH2:4][OH:5]

参加物

4

反応物 2

HCID 160976-Methyl-2-nitrobenzoic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 12204069(2-Methyl-6-nitrophenyl)methanol収率 107.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 100 mL round bottomed flask under dry argon was charged with 5 g of 2-methyl-6-nitrobenzoic acid which was dissolved in 60 mL of dry tetrahydrofuran. To this solution was added slowly with cooling and stirring, 64.17 mL of a 1M solution of BH3.THF in THF. The mixture was refluxed for 17 h then the reaction was slowly and carefully quenched with an excess of 10% aqueous hydrochloric acid. The THF was removed under vacuum and the residue was extracted with three 50 mL aliquots of methylene chloride. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and the solvent removed. The crude product was recrystallized from methylene chloride/pentane to give 4.95 g of yellowish crystals (97% yield).

後処理

  1. additionTo this solution was added slowly
  2. temperaturewith cooling
  3. temperatureThe mixture was refluxed for 17 h
  4. customcarefully quenched with an excess of 10% aqueous hydrochloric acid
  5. customThe THF was removed under vacuum
  6. extractionthe residue was extracted with three 50 mL aliquots of methylene chloride
  7. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed
  10. customThe crude product was recrystallized from methylene chloride/pentane

出典と根拠

ORDレコード
ord-e01606a0026d4463b5f5c69118422b29
出典データセット
uspto-grants-1993_04
特許番号
US05200544

反応ノート

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