1-(2-Hydroxy-5-methoxyphenyl)ethan-1-one → 2-(2-Hydroxypropan-2-YL)-4-methoxyphenol

HRID 81778

反応式

HRID 81778 の反応式
[CH3:1][Mg]Br.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[C:13](=[O:15])[CH3:14]>C1COCC1>[OH:15][C:13]([C:6]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=1[OH:4])([CH3:1])[CH3:14]

参加物

4

反応物 2

HCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-oneHCID 178418573HCID 178418573、化合物

生成物 1

HCID 252417532-(2-Hydroxypropan-2-YL)-4-methoxyphenol収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methylmagnesium bromide (221 ml, 665 mmol) in 800 ml THF at 0° C. was added 1-(2-hydroxy-5-methoxy-phenyl)-ethanone (20.21 g, 302 mmol) in portions over 30 min. The mixture was allowed to warm to room temperature. After 16 h the mixture was quenched by the slow addition of 10% NH4Cl, carefully acidified to pH=1 (slow addition) with concentrated HCl and extracted with Et2O. The combined organics were washed with H2O, washed with brine, died over MgSO4, filtered and concentrated in vacuo to give 2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-phenol (50.57 g, 100%) as a tan solid.

後処理

  1. customAfter 16 h the mixture was quenched by the slow addition of 10% NH4Cl
  2. additioncarefully acidified to pH=1 (slow addition) with concentrated HCl
  3. extractionextracted with Et2O
  4. washThe combined organics were washed with H2O
  5. washwashed with brine
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-73b9d656da9d4f0aa377f6f630857760
出典データセット
uspto-grants-2014_09
特許番号
US08846705B2

関連ノート

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