Chloroform → Hydrochloric Acid

HRID 233352

반응식

HRID 233352 반응식
CC1C=C(N[C:10](=[O:19])CC2C=CC(O)=CC=2)C=C(C)C=1.[OH-:20].[Na+].[C:22]1(=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(Cl)(Cl)[Cl:30]>C1COCC1>[ClH:30].[CH:22]1([C:10]([OH:19])=[O:20])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

참가 물질

7

반응물 4

HCID 6212ChloroformHCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 2763537N-(3,5-dimethylphenyl)-2-(4-hydroxyphenyl)acetamide

생성물 2

HCID 313Hydrochloric AcidHCID 7413Cyclohexanecarboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (3.06 gms, 12 mmol) in THF is treated with 2.4 gms (60 mmol) of NaOH at -20° C. Subsequently 5,889 gms (60 mmol) of cyclohexanone and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirred overnight at room temperature. THF is removed under vacuum and the residue is dissolved in water, followed by acidification with 35% HCl. The precipitated solid is extracted into ether and treated with 6% sodium bicarbonate solution. The aqueous layer on acidification with HCl yields the product 1-[4-(((3,5-dimethylphenyl)amino)carbonyl) methyl)phenoxy]cyclohexanecarboxylic acid (C23H27NO4). The product was purified by repeated extraction into ether and NaHCO3.

후처리

  1. customTHF is removed under vacuum
  2. dissolutionthe residue is dissolved in water
  3. extractionThe precipitated solid is extracted into ether
  4. additiontreated with 6% sodium bicarbonate solution

출처 및 근거

ORD 기록
ord-4b35b438b8a64f9da346dc280d97fc6f
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591892

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