Pyridine → HCID 23126010, compound

HRID 132737Notes

Reaction equation

HRID 132737 reaction equation
[CH2:1]([C:5]([CH2:10][CH:11]([CH3:13])[CH3:12])([CH2:8][OH:9])[CH2:6][OH:7])[CH:2]([CH3:4])[CH3:3].[O:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.N1C=C[CH:22]=[CH:21][CH:20]=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[C:18]([O:9][CH2:8][C:5]([CH2:10][CH:11]([CH3:13])[CH3:12])([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:6][O:7][C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 39856252,2-Diisobutyl-1,3-propanediol

Product 1

HCID 23126010HCID 23126010, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7.5 g (0.04 mol) 2,2-diisobutyl-1,3-propandiol was added 50 ml tetrahydrofuran, then added 9.7 ml (0.12 mol) pyridine with stirring. To the resulting homogenous mixture was slowly added 11.6 ml (0.1 mol) benzoyl chloride. The mixture was stirred at room temperature for 1 hour, and heated refluxing for 5 hours. Upon completing the reaction, 40 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 2,2-diisobutyl-1,3-propandiol dibenzoate as a pale yellow liquid, the yield was 93%.

Workup

  1. stirringThe mixture 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-af2ac3dc5dd947b3a85b59d1d0d175ca
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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