Pyridine → 2,5-Hexanediol dibenzoate

HRID 132741

Reaction equation

HRID 132741 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 52594462,5-Hexanediol dibenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-c7485da0c3a449b786a71169a14152f2
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Linked notes

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