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

HRID 630398ノート

反応式

HRID 630398 の反応式
[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]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 21536136Benzoic acid, 5-chloro-4-hydroxy-2-methoxy-, methyl ester2 回

生成物 1

HCID 671453092-Chloro-4-(hydroxymethyl)-5-methoxyphenol収率 34%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-be4881ac89084a83aa7705c9f3def052
出典データセット
uspto-grants-2016_04
特許番号
US09315463B2

反応ノート

読み込み中…