Aluminium lithium hydride → 2-Chloro-4-(hydroxymethyl)-5-methoxyphenol

HRID 630398노트

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HRID 630398 반응식
[Cl:1][C:2]1[C:3]([OH:14])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:6]([CH2:7][OH:8])[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[OH:14]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 21536136Benzoic acid, 5-chloro-4-hydroxy-2-methoxy-, methyl ester2회

생성물 1

HCID 671453092-Chloro-4-(hydroxymethyl)-5-methoxyphenol수율 34%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of methyl 5-chloro-4-hydroxy-2-methoxybenzoate (intermediate 53; 204 mg; 0.94 mmol) in 4.6 ml of anhydrous THF was stirred with external ice/water bath cooling. A solution of 1M LiAlH4 in THF was dropped in (1.9 ml; 1.9 mmol). After 5 minutes the external bath was removed and the stirring prosecuted for 3 additional hours. With external cooling 0.072 ml of water were added followed by 0.072 ml of 4N NaOH solution and 0.144 additional ml of water. After filtration the cake was thoroughly washed with THF and the filtrates were concentrated giving the title compound in 34% yield.

후처리

  1. temperaturecooling
  2. customAfter 5 minutes the external bath was removed
  3. temperatureWith external cooling 0.072 ml of water
  4. additionwere added
  5. filtrationAfter filtration the cake
  6. washwas thoroughly washed with THF
  7. concentrationthe filtrates were concentrated

출처 및 근거

ORD 기록
ord-be4881ac89084a83aa7705c9f3def052
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315463B2

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