Ethylene Glycol → Tertiary butoxymethyl diethylene glycol

HRID 127665

Reaction equation

HRID 127665 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[CH3:5][C:6]([O:9][CH2:10][CH:11]1[O:13][CH2:12]1)([CH3:8])[CH3:7].[OH-].[Na+]>B(F)(F)F.CCOCC.ClCCl>[C:6]([O:9][CH2:10][CH:11]([OH:13])[CH2:12][O:3][CH2:2][CH2:1][OH:4])([CH3:5])([CH3:7])[CH3:8]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 243142-((1,1-Dimethylethoxy)methyl)oxirane

Product 1

HCID 20285608Tertiary butoxymethyl diethylene glycolYield 71%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethylene glycol (248 g, 4 moles) and boron trifluoride etherate catalyst (1 ml) in dichloromethane (20 ml) preheated to 45° C. was added t-BGE (130 g, 1 mole) dropwise at such a rate so as to maintain a gentle reflux. After completion of addition, stirring was continued for about 15 hours. The solution was then adjusted to pH 7.5 by addition of sodium hydroxide and the product removed by distillation. Tertiary butoxymethyl diethylene glycol was obtained in 71 percent yield having a boiling point of 105° C.-115° C./1 mm.

Workup

  1. custompreheated to 45° C.
  2. temperatureto maintain a gentle reflux
  3. additionAfter completion of addition
  4. customthe product removed by distillation

Sources & evidence

ORD record
ord-203857138ae24d558113da98a74e02ca
Source dataset
uspto-grants-1981_03
Patent number
US04256859

Linked notes

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