Ethylene Glycol → 2-[2-(Methylsulfanyl)ethyl]-1,3-dioxolane

HRID 262010Notes

Reaction equation

HRID 262010 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH:5]=[O:6].[CH2:7](O)[CH2:8][OH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.O1CCOCC1.C1C=CC=CC=1>[CH3:1][S:2][CH2:3][CH2:4][CH:5]1[O:9][CH2:8][CH2:7][O:6]1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 18635Methional

Product 1

HCID 203986662-[2-(Methylsulfanyl)ethyl]-1,3-dioxolane

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1040 g (10 moles) of freshly distilled methional, 650 g (10.5 moles) of ethylene glycol, 400 cc of benzene, 800 cc of dioxan and 10 g of p-toluene sulphonic acid are heated under reflux until the azeotropic entrainment of the water formed during the reaction, which takes 2 hours, is over. The acid medium is then neutralised by the addition of 10 g of dry sodium carbonate, after which the solution is concentrated to dryness in a water pump vacuum.

Workup

  1. customformed during the reaction, which
  2. concentrationafter which the solution is concentrated to dryness in a water pump vacuum

Sources & evidence

ORD record
ord-7ea0a2b840064fc5ad51be1b47b959b2
Source dataset
uspto-grants-1979_05
Patent number
US04153442

Reaction notes

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