Pyridine → 2,4-Pentanediol, dibenzoate

HRID 1751146Notes

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

Participants

Reactant 4

HCID 1049Pyridine

HCID 7412Benzoyl chloride

HCID 8028Tetrahydrofuran

HCID 122622,4-Pentanediol

Product 1

HCID 122658152,4-Pentanediol, dibenzoateYield 95%

Procedure

Into 3.1 g (0.03 mol) 2,4-pentanediol, 30 ml THF and 7.1 g (0.09 mol) pyridine are added, and 10.5 g (0.075 mol) benzoyl chloride is added under stirring, then a heat-reflux is carried out for 4 h. After cooling, 20 ml saturated salt solution is added, then extraction is carried out with ethyl acetate, and after drying with anhydrous NaSO4, the solvent is removed. A colourless liquid of 8.9 g 2,4-pentanediol dibenzoate is obtained by column chromatography. The yield is 95%.

Workup

temperatureAfter cooling
extractionextraction
dry with materialafter drying with anhydrous NaSO4
customthe solvent is removed

Sources & evidence

ORD record: ord-ed950b74f5954379a5ba39cc060d2b2f
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156927B2

Reaction notes

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