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Sodium Hydroxide → 1,4-Diethoxynaphthalene-2,3-dicarboxylic acid

HRID 583908
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HRID 583908 반응식
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH3:16])=[C:6]([C:17]([O-:19])=[O:18])[C:5]=1[C:20]([O:22]CC)=[O:21])[CH3:2].[OH-].[Na+]>C(O)C.O>[CH2:15]([O:14][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:20]([OH:22])=[O:21])[C:6]=1[C:17]([OH:19])=[O:18])[CH3:16]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 86592169Ethyl 1,4-diethoxy-2,3-naphthalenedicarboxylate

생성물 1

HCID 223445251,4-Diethoxynaphthalene-2,3-dicarboxylic acid수율 92.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

Ethyl 1,4diethoxy-2,3-naphthalenedicarboxylate (32 g, 89 mmol) was added to a solution of sodium hydroxide (20 g) in ethanol (200 ml) and water (40 ml) and stirred for 1.5 h at 60° C. The reaction was cooled and the thick white suspension was filtered. The solid was dissolved in a mixture of ethyl acetate (200 ml) and water (800 ml). The layers were separated and the aqueous was acidified with hydrochloric acid (2M, 120 ml). The aqueous was extracted with ethyl acetate (2×) and the combined organics were dried (MgSO4). Evaporation of the solvent under vacuum gave the title compound as a white solid (25 g, 92%). δH [2H6]—DMSO 13.26,(2H, s), 8.15,(2H, m), 7.72,(2H, m), 4.13,(4H, q), 1.42,(6H, t).

후처리

  1. temperatureThe reaction was cooled
  2. filtrationthe thick white suspension was filtered
  3. dissolutionThe solid was dissolved in a mixture of ethyl acetate (200 ml) and water (800 ml)
  4. customThe layers were separated
  5. extractionThe aqueous was extracted with ethyl acetate (2×)
  6. dry with materialthe combined organics were dried (MgSO4)
  7. customEvaporation of the solvent under vacuum

출처 및 근거

ORD 기록
ord-d43cc72eea124f52ac241f129d75e50b
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06924297B2

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