Pyridine → 1,2-butandiol Dibenzoate

HRID 132707

Reaction equation

HRID 132707 reaction equation
[CH2:1]([OH:6])[CH:2]([OH:5])[CH2:3][CH3:4].[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=C[CH:19]=[CH:18][CH:17]=1.[O:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>O>[C:7]([O:6][CH2:1][CH:2]([O:5][C:26](=[O:22])[C:25]1[CH:19]=[CH:18][CH:17]=[CH:23][CH:24]=1)[CH2:3][CH3:4])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 114291,2-Butanediol

Product 1

HCID 231259061,2-butandiol Dibenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the reactor were added 1,2-butylene-glycol (2.5 g), benzoyl chloride (7.8 g), pyridine (8.8 g) and tetrahydrofuran (70 ml). The reactants was mixed and heated refluxing for 4 hours, then cooled to room temperature. Water was added to the reaction system until the inorganic phase was transparent. Organic phase was separated. Inorganic phase was extracted with ethyl ether. The combined organic phase was washed with water, dried over anhydrous sodium sulfate. After concentrated, 3.95 g product was separated. 1H-NMR: δ (ppm)1.0-1.1 (3H), 1.7-1.9(2H), 4.4-4.6(2H), 5.4-5.5(1H) and 7.4-8.2(10H).

Workup

  1. additionThe reactants was mixed
  2. temperatureheated
  3. temperaturerefluxing for 4 hours
  4. customOrganic phase was separated
  5. extractionInorganic phase was extracted with ethyl ether
  6. washThe combined organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationAfter concentrated
  9. custom3.95 g product was separated

Sources & evidence

ORD record
ord-b78bc78a8a854a8a814d4a63cfdec3ef
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Linked notes

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