Pyridine → 2,4-Pentanediol, dibenzoate

HRID 132709

Reaction equation

HRID 132709 reaction equation
[CH3:1][CH:2]([OH:7])[CH2:3][CH:4]([OH:6])[CH3:5].N1C=C[CH:11]=[CH:10][CH:9]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>>[C:14]([O:6][CH:4]([CH2:3][CH:2]([O:7][C:27](=[O:23])[C:26]1[CH:11]=[CH:10][CH:9]=[CH:24][CH:25]=1)[CH3:1])[CH3:5])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 122622,4-Pentanediol

Product 1

HCID 122658152,4-Pentanediol, dibenzoateYield 95%

Procedure

To 3.1 g (0.03 mol) 2,4-pentanediol were added 30 ml tetrahydrofuran and 7.1 g (0.09 mol) pyridine, then added 10.5 g (0.075 mol) benzoyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled and added 20 ml saturated saline. The reaction mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate, filtered. After removing solvent, the crude was purified by column chromatography to give 8.9 g 2,4-pentanediol dibenzoate as a colorless liquid, the yield was 95%.

Workup

  1. temperatureThe reaction was heated
  2. temperaturerefluxing for 4 hours
  3. temperaturecooled
  4. additionadded 20 ml saturated saline
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customAfter removing solvent
  9. customthe crude was purified by column chromatography

Sources & evidence

ORD record
ord-609a346c765a4625b438a18e689450bc
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Linked notes

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