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Hydrochloric Acid → HCID 22722091, 화합물

HRID 1581682
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HRID 1581682 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])(=[O:3])[CH3:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22722095HCID 22722095, 화합물

생성물 1

HCID 22722091HCID 22722091, 화합물수율 49.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of methyl 2-(3-acetamidophenoxy)benzoate (4.7 g crude mixture) in dioxane (100 mL) was added 1.0 N NaOH (24 mL). After stirring at RT for 72 hr the reaction was acidified with 1.0 N HCl (24 mL) and extracted with EtOAc. The combined organic layers were washed with brine, dried (Mg SO4), and concentrated. The residue was purified by flash chromatography on silica gel (95:4:1 CHCl3/MeOH/AcOH) to give the crude title compound (2.2 g, 34%) as a beige solid: MS (ES) m/e 272.2 (M+H)+. The title compound prepared in this way contained approximately 46% of the diacid resulting from the di-ester starting material contaminant: MS (ES) m/e 392.2 (M+H)+. The mixture was used without further purification.

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Mg SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (95:4:1 CHCl3/MeOH/AcOH)

출처 및 근거

ORD 기록
ord-72a9672592a843a3b17ebf54894f6fa6
출처 데이터셋
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06730684B1

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