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

HRID 221940ノート

反応式

HRID 221940 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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%).

後処理

  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))

出典と根拠

ORDレコード
ord-e85984ff35954054bdef9474740e5d07
出典データセット
uspto-grants-2012_06
特許番号
US08207134B2

反応ノート

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