Hydrochloric Acid → 3-Chloro-4-hydroxybenzyl alchol

HRID 911446노트

반응식

HRID 911446 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 2574563-Chloro-4-hydroxybenzyl alchol

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-088128e025b7472ca00d83226fadbca9
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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