Pyridine → 2,5-Hexanediol dibenzoate

HRID 132741

반응식

HRID 132741 반응식
[CH3:1][CH:2]([OH:8])[CH2:3][CH2:4][CH:5]([OH:7])[CH3:6].[O:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.N1C=C[CH:17]=[CH:16][CH:15]=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[C:13]([O:7][CH:5]([CH2:4][CH2:3][CH:2]([O:8][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:1])[CH3:6])(=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:10][CH:11]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 180492,5-Hexanediol

생성물 1

HCID 52594462,5-Hexanediol dibenzoate수율 94%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 2.4 g (0.02 mol) 2,5-hexanediol was added 30 ml tetrahydrofuran, then added 4.8 ml (0.06 mol) pyridine with stirring. To the resulting homogenous mixture was slowly added 5.8 ml (0.05 mol) benzoyl chloride, and the reaction was stirred at room temperature for 1 hour, then heated refluxing for 5 hours. Upon completing the reaction, 20 ml water was added to dissolve the resulting salt. The mixture was extracted with ethyl acetate. The organic phase was separated, washed with saturated saline for two times, and dried over anhydrous sodium sulfate. The solvent was removed. Distillation under reduced pressure gave colorless liquid 2,5-hexanediol dibenzoate, and the yield was 94%. 1HNMR: δ (ppm) 1.36(d, 6H, CH3), 1.86(m, 4H, CH2), 5.21(m, 2H, CH), 7.40-8.16(m, 10H, ArH)

후처리

  1. stirringthe reaction was stirred at room temperature for 1 hour
  2. temperatureheated
  3. temperaturerefluxing for 5 hours
  4. additionwas added
  5. dissolutionto dissolve the resulting salt
  6. extractionThe mixture was extracted with ethyl acetate
  7. customThe organic phase was separated
  8. washwashed with saturated saline for two times
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed
  11. distillationDistillation under reduced pressure

출처 및 근거

ORD 기록
ord-c7485da0c3a449b786a71169a14152f2
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388061B2

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