Pyridine → 1-Chloro-3,6,9-trioxadecane

HRID 2292307Notes

Reaction equation

HRID 2292307 reaction equation
[CH2:1](O)[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH3:10].S(Cl)([Cl:14])=O.N1C=CC=CC=1>O1CCCC1>[CH2:1]([Cl:14])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8178Triethylene glycol monomethyl etherHCID 24386Thionyl Chloride

Product 1

HCID 5478521-Chloro-3,6,9-trioxadecaneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

101.16 g (≈0.6 mole) of 3,6,9-trioxadecanol are reacted with 44.6 ml (≈0.6 mole) of thionyl chloride and 51.7 ml (≈0.64 mole) of pyridine in a tetrahydrofuran solution by refluxing for 12 hours to give 3,6,9-trioxadecyl chloride ##STR19## The mixture is cooled and then extracted several times with methyl ethyl ketone (MEK), and the MEK phase is then neutralized with NaHCO3 and dried over Na2SO4. After the MEK has been removed, the residue is distilled under 30 Pa and at 30°-37° C. Yield: 90%.

Workup

  1. temperatureby refluxing for 12 hours

Sources & evidence

ORD record
ord-7e18f828607143b998469f243af91a8a
Source dataset
uspto-grants-1989_01
Patent number
US04801734

Reaction notes

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