Hydrochloric Acid → 2,5,9,12-Tetraoxatridecan-7-ol

HRID 567644Notes

Reaction equation

HRID 567644 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[OH-].[Na+].[CH3:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH:14]1[O:16][CH2:15]1.Cl>CC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:15][CH:14]([OH:16])[CH2:13][O:12][CH2:11][CH2:10][O:9][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 14798Sodium Hydroxide2×HCID 2347342-((2-Methoxyethoxy)methyl)oxirane

Product 1

HCID 148932732,5,9,12-Tetraoxatridecan-7-olYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

To ethylene glycol monomethyl ether (86.4 g, 2.27 moles), ground caustic soda (16.7 g, 0.83 moles) was added by several portions and caustic soda was dissolved by heating to 80° C. Ethylene glycol glycidyl methyl ether (50 g, 0.76 moles) was then added dropwise. After the completion of the dropwise addition, the solution was stirred for 2 hours and then air-cooled at room temperature. The solution was neutralized with hydrochloric acid and a salt was deposited by adding acetone, followed by filtration. Low-boiling materials were removed under reduced pressure to obtain 67 g (yield 85%) of 1,3-bis(2-methoxyethoxy)-2-propanol.

Workup

  1. dissolutionwas dissolved
  2. additionAfter the completion of the dropwise addition
  3. temperatureair-cooled at room temperature
  4. filtrationfollowed by filtration
  5. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-b57ab0857f8a43b79376294d8d1e38af
Source dataset
uspto-grants-2001_01
Patent number
US06180287B2

Reaction notes

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