Pyridine → 2-Methyl-2,4-pentanediol dibenzoate

HRID 132711

Reaction equation

HRID 132711 reaction equation
[CH3:1][C:2]([OH:8])([CH2:4][CH:5]([OH:7])[CH3:6])[CH3:3].N1C=C[CH:12]=[CH:11][CH:10]=1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[C:15]([O:8][C:2]([CH3:3])([CH2:4][CH:5]([O:7][C:28](=[O:24])[C:27]1[CH:12]=[CH:11][CH:10]=[CH:25][CH:26]=1)[CH3:6])[CH3:1])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 7870Hexylene GlycolHCID 8028Tetrahydrofuran

Product 1

HCID 193919182-Methyl-2,4-pentanediol dibenzoateYield 88%

Procedure

To 0.03 mol 2-methyl-2,4-pentanediol were added 30 ml tetrahydrofuran and 0.09 mol pyridine, then added 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 2-methyl-2,4-pentanediol dibenzoate as a colorless liquid, and the yield was 88%.

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-e577ef99881a4f6d9be847a415bff470
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Linked notes

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