3-Methylnaphthalene-2-carboxylic acid → (3-Methylnaphthalen-2-yl)methanol

HRID 330521노트

반응식

HRID 330521 반응식
[CH3:1][C:2]1[C:3]([C:12](O)=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[C:3]([CH2:12][OH:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

4

반응물 2

HCID 198686763-Methylnaphthalene-2-carboxylic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 14699377(3-Methylnaphthalen-2-yl)methanol수율 99.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution of 3-methyl-2-naphthoic acid (5.0 g, 26.9 mmol) in anhydrous THF (75 mL) was cooled to 0° C. and treated with lithium aluminum hydride (1M in THF, 26.9 mL, 26.9 mmol) added dropwise. After the addition was complete, the resulting mixture was stirred 5 minutes at 0° C., the ice bath was removed, the mixture warmed to room temperature and stirred a total of 20 hours. The mixture was cooled to 0° C. and quenched by dropwise addition of water (1.02 mL), followed by 15% NaOH (1.02 mL), and more water (3 mL). The resulting mixture was stirred 1 hour and the granular precipitate removed by filtration through a plug of Florosil and anhydrous magnesium sulfate. The filtrate was concentrated in vacuo, to give the desired product (4.6 g, 99%) as a white crystalline solid of sufficient purity for use in the subsequent reaction.

후처리

  1. additionadded dropwise
  2. additionAfter the addition
  3. customthe ice bath was removed
  4. temperaturethe mixture warmed to room temperature
  5. stirringstirred a total of 20 hours
  6. temperatureThe mixture was cooled to 0° C.
  7. customquenched by dropwise addition of water (1.02 mL)
  8. stirringThe resulting mixture was stirred 1 hour
  9. customthe granular precipitate removed by filtration through a plug of Florosil and anhydrous magnesium sulfate
  10. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-5d0a018efdcd4f4b87bd50640dfa4d04
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04897405

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