Oxygen → 3-ethyl-2,4-pentanediol Dibenzoate

HRID 132720Notes

Reaction equation

HRID 132720 reaction equation
O=O.[CH2:3]([CH:5]([CH:9]([OH:11])[CH3:10])[CH:6]([OH:8])[CH3:7])[CH3:4].N1C=C[CH:15]=[CH:14][CH:13]=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>N#N.O>[C:18]([O:8][CH:6]([CH:5]([CH2:3][CH3:4])[CH:9]([O:11][C:29](=[O:30])[C:28]1[CH:27]=[CH:31][CH:15]=[CH:14][CH:13]=1)[CH3:10])[CH3:7])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 977OxygenHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 218678653-Ethyl-2,4-pentanediol

Product 1

HCID 231259023-ethyl-2,4-pentanediol Dibenzoate

Reagents, catalysts & solvents 2

HCID 947NitrogenSolventHCID 962WaterSolvent

Procedure

In N2 atmosphere free of water and oxygen, to a reactor were successively added 0.02 mol 3-ethyl-2,4-pentanediol, 20 ml THF, and 0.06 mol pyridine, then slowly added dropwise 0.05 mol benzoyl chloride. The reaction was heated refluxing for 8 hours, and allowed to continue at room temperature for further 12 hours. After the reaction was finished, the reaction mixture was filtered and the cake was washed with anhydrous ethyl ether for three times. The organic phase was completely washed with saturated saline, and dried over anhydrous sodium sulfate. Removing the solvent gave 5.1 g product.

Workup

  1. temperatureThe reaction was heated
  2. temperaturerefluxing for 8 hours
  3. filtrationthe reaction mixture was filtered
  4. washthe cake was washed with anhydrous ethyl ether for three times
  5. washThe organic phase was completely washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRemoving the solvent

Sources & evidence

ORD record
ord-8f2f5528e6f94937a17744271aec00d2
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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