Sulfuric Acid → Naphthalene-1,4-dicarboxylic acid diisopropyl ester

HRID 221940노트

반응식

HRID 221940 반응식
S(=O)(=O)(O)O.[C:6]1([C:19]([OH:21])=[O:20])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(O)C>[CH:6]([O:17][C:16]([C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([C:19]([O:21][CH:9]([CH3:10])[CH3:8])=[O:20])=[CH:7][CH:8]=1)=[O:18])([CH3:15])[CH3:7]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 690651,4-Naphthalenedicarboxylic acid

생성물 1

HCID 57332763Naphthalene-1,4-dicarboxylic acid diisopropyl ester수율 76.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

Under a nitrogen stream, sulfuric acid (8 mL) was added dropwise over 3 hours to a solution of naphthalene-1,4-dicarboxylic acid (1.107 g, 5.12 mmol) in 2-propanol (60 mL) while heating to reflux. The resultant solution was cooled to room temperature and then saturated aqueous sodium carbonate was added thereto. The mixture was then stirred for 10 minutes at room temperature. The resultant mixture was twice extracted with dichloromethane. After drying the organic layer over anhydrous magnesium sulfate, solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (15:85)), to thereby obtain the titled compound (588 mg, 38%).

후처리

  1. temperaturewhile heating to reflux
  2. extractionThe resultant mixture was twice extracted with dichloromethane
  3. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate, solvent
  4. customwas removed by distillation under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (15:85))

출처 및 근거

ORD 기록
ord-e85984ff35954054bdef9474740e5d07
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207134B2

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