Hydrochloric Acid → [1,1'-Biphenyl]-3-methanol, 2-methyl-

HRID 1065556

反応式

HRID 1065556 の反応式
[CH3:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[ClH:13].[OH-].[K+]>[Fe].C(O)C>[CH3:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:6][CH:7]=[CH:8][C:9]=1[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:3]=1.[ClH:13].[OH:5][CH2:4][C:3]1[C:2]([CH3:1])=[C:9]([CH:8]=[CH:7][CH:6]=1)[NH2:10]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 902892-Methyl-3-nitrobenzyl alcohol

生成物 2

HCID 596875[1,1'-Biphenyl]-3-methanol, 2-methyl-HCID 20270659(3-Amino-2-methylphenyl)methanol hydrochloride

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

2-Methyl[1,1'-biphenyl]-3-methanol was prepared as follows: To 100 ml of stirred 50% aqueous ethanol was added 2-methyl-3-nitrobenzyl alcohol (41.8 g, 0.25 mole) and 85.0 grams of iron powder. The mixture was brought to reflux, and 5.2 ml of concentrated hydrochloric acid was slowly added. Upon complete addition, the reaction mixture was stirred under reflux for 2 hours. The reaction mixture was then made just basic with ethanolic 15% potassium hydroxide. The hot mixture was filtered through diactomaceous earth to remove the iron. The filter cake was washed with ethanol. The filtrate was acidified with hydrogen chloride, then allowed to stand at room temperature for 16 hours. The ethanol was removed by evaporation under reduced pressure. Hexane was added to the residue, and the water-hexane azeotrope was removed by distillation. The addition of hexane and the subsequent removal of the water-hexane azeotrope by distillation was repeated three times. The 3-hydroxymethyl-2-methylaniline hydrochloride residue thus obtained was used as follows.

後処理

  1. temperatureto reflux
  2. additionUpon complete addition
  3. temperatureunder reflux for 2 hours
  4. filtrationThe hot mixture was filtered through diactomaceous earth
  5. customto remove the iron
  6. washThe filter cake was washed with ethanol
  7. customThe ethanol was removed by evaporation under reduced pressure
  8. additionHexane was added to the residue
  9. customthe water-hexane azeotrope was removed by distillation
  10. additionThe addition of hexane
  11. customthe subsequent removal of the water-hexane azeotrope
  12. distillationby distillation

出典と根拠

ORDレコード
ord-d86913fc311c4f90af08a9f9532b4fa1
出典データセット
uspto-grants-1982_05
特許番号
US04329518

関連ノート

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