p-Toluenesulfonic acid → cis-1,3-Cyclohexanedicarboxylic acid diethyl ester

HRID 321908ノート

反応式

HRID 321908 の反応式
[C@H:1]12[C:10](=O)[O:9][C:7](=[O:8])[C@H:3]([CH2:4][CH2:5][CH2:6]1)[CH2:2]2.[CH:12]([O:19]CC)([O:16][CH2:17][CH3:18])OCC.[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[C@H:5]1([C:12]([O:16][CH2:17][CH3:18])=[O:19])[CH2:6][CH2:1][CH2:2][C@@H:3]([C:7]([O:9][CH2:10][CH3:22])=[O:8])[CH2:4]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 11367118cis-1,3-Cyclohexanedicarboxylic anhydride

生成物 1

HCID 10977233cis-1,3-Cyclohexanedicarboxylic acid diethyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

Anhydride 1 (7.71 g; 50 mmol) was combined with triethyl orthoformate (12.5 mL; 75 mmol; 1.5 equiv) and ethanol (50 mL). p-Toluenesulfonic acid (0.48 g; 2.5 mmol; 0.05 equiv) was added and the reaction mixture was heated overnight at 60° C. to completely consume 1. Solid sodium bicarbonate (0.5 g) was added and the solvent was removed at reduced pressure. The residue was dissolved in toluene (25 mL), washed with saturated aqueous NaHCO3 (5 mL), dried over Na2SO4, and concentrated to afford 11.42 g (99%) of cis-2b which was a single peak by GC analysis.

後処理

  1. customto completely consume 1
  2. additionSolid sodium bicarbonate (0.5 g) was added
  3. customthe solvent was removed at reduced pressure
  4. dissolutionThe residue was dissolved in toluene (25 mL)
  5. washwashed with saturated aqueous NaHCO3 (5 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto afford 11.42 g (99%) of cis-2b which

出典と根拠

ORDレコード
ord-103a8571befd42b9b33d9e2537247ea4
出典データセット
uspto-grants-2001_04
特許番号
US06210956B1

反応ノート

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