Methyl 3-amino-4-methylbenzoate → (3-Amino-4-methylphenyl)methanol

HRID 1090635

反応式

HRID 1090635 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5](OC)=[O:6].[BH4-].[Li+]>COCCOCCOC>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[CH2:5][OH:6]

参加物

4

反応物 2

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 4148881Lithium borohydride2 回

生成物 1

HCID 586243(3-Amino-4-methylphenyl)methanol収率 54%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

実験手順

Methyl 3-amino-4-methylbenzoate (16.52 g, 0.1 mol) was dissolved in diglyme (150 ml), lithium borohydride (2.18 g, 0.1 mol) added, and the solution stirred at room temperature overnight. A further portion of lithium borohydride (2.18 g, 0.1 mol) was added, and the mixture heated at reflux for 20 minutes. The reaction was quenched with water, the solvent evaporated, the residue dissolved in water, the solution adjusted to pH 5 with hydrochloric acid, and the product extracted into dichloromethane. Drying, evaporation and trituration with ether gave 3-amino-4-methylbenzyl alcohol (7.3 g, 54%), m.p. 105°-107°.

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 20 minutes
  3. customThe reaction was quenched with water
  4. customthe solvent evaporated
  5. dissolutionthe residue dissolved in water
  6. extractionthe product extracted into dichloromethane
  7. customDrying
  8. customevaporation and trituration with ether

出典と根拠

ORDレコード
ord-2876b2df4dc640f6a5c36e0b061b89c4
出典データセット
uspto-grants-1992_01
特許番号
US05082848

関連ノート

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