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

HRID 321908노트

반응식

HRID 321908 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-103a8571befd42b9b33d9e2537247ea4
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06210956B1

반응 노트

불러오는 중…