Hydrochloric Acid → 3-Chloro-4-hydroxybenzyl alchol

HRID 911446ノート

反応式

HRID 911446 の反応式
CC(C[AlH]CC(C)C)C.[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[OH:21])[C:14](OC)=[O:15].Cl>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[OH:21])[CH2:14][OH:15]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 77580Methyl 3-chloro-4-hydroxybenzoate

生成物 1

HCID 2574563-Chloro-4-hydroxybenzyl alchol

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Add a solution of DIBAL-H in toluene (1.0 M, 35 mL) to a solution of methyl 3-chloro-4-hydroxybenzoate (1.9 g, 10 mmol) at 0° C. under nitrogen. Stir the reaction at 0° C. and gradually warm to ambient temperature overnight. Quench the reaction with slow addition of 0.1N aqueous HCl, add more acid to break the gel-like solid to two clear layers. Separate the organic layer, and extract the aqueous layer with EtOAc three times. Combine the organic layers, wash with brine, dry over Na2SO4, filter and concentrate to give a white solid. MS (ES−) m/z 157 (M−H)−.

後処理

  1. customthe reaction at 0° C.
  2. customQuench
  3. customthe reaction
  4. additionadd more acid
  5. customSeparate the organic layer
  6. extractionextract the aqueous layer with EtOAc three times
  7. washCombine the organic layers, wash with brine
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customto give a white solid

出典と根拠

ORDレコード
ord-088128e025b7472ca00d83226fadbca9
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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