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

HRID 1090635

반응식

HRID 1090635 반응식
[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]

참가 물질

4

반응물 2

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 4148881Lithium borohydride2회

생성물 1

HCID 586243(3-Amino-4-methylphenyl)methanol수율 54%

시약·촉매·용매 1

HCID 8150Diglyme용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-2876b2df4dc640f6a5c36e0b061b89c4
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082848

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