Formaldehyde → 2,5,7,10-Tetraoxaundecane

HRID 1683448Notes

Reaction equation

HRID 1683448 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[CH2:6]=[O:7]>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:4][CH2:3][O:2][CH3:1]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 80192-Methoxyethanol

Product 1

HCID 781642,5,7,10-TetraoxaundecaneYield 71.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

1045 g of 2-methoxyethanol (Mr =76,1), 194 g of paraformaldehyde (Mr =30.03 based on formaldehyde) and 16 g of p-toluenesulfonic acid (Mr =172.2) are reacted for 2 hours at 90° C. The water of reaction is then removed by distillation. The reaction mixture is distilled under reduced pressure (c. 20 mbar), affording 758 g of bis(2-methoxyethoxy)methane (Mr =164.21) in c. 99% purity, yield: 67% of theory. The remainder (33%) consists almost completely of the educt, which can be recycled, so that total yields of over 97% result.

Workup

  1. customis then removed by distillation
  2. distillationThe reaction mixture is distilled under reduced pressure (c. 20 mbar)

Sources & evidence

ORD record
ord-e5b919a52a04407893e4c887b165e30a
Source dataset
uspto-grants-1997_06
Patent number
US05637775

Reaction notes

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