Diethylene Glycol → HCID 117716545, compound

HRID 1398270Notes

Reaction equation

HRID 1398270 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][Br:8])=[O:16]

Participants

5

Reactant 2

HCID 8117Diethylene GlycolHCID 202106-Bromohexanoic acid

Product 1

HCID 117716545HCID 117716545, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

Into a 3-liter 4-neck round bottom flask equipped with a mechanical stirrer was added a solution of diethylene glycol (100 g), 6-bromo hexanoic acid (386 g) and para-toluene sulphonic acid (5 g) in toluene (1000 ml). The solution was refluxed for 3 hours using a Dean-Stark apparatus with azeotropic removal of water. The solution was cooled to room temperature. The toluene layer was washed with 5% sodium bicarbonate solution (1500 ml) and water (1000 ml). The solution was dried over anhydrous sodium sulphate and distilled to obtain 6-bromohexanoic acid 2-[2-(6-bromohexanoyloxy)-ethoxy]-ethyl ester (400 g) as light yellow oil.

Workup

  1. customInto a 3-liter 4-neck round bottom flask equipped with a mechanical stirrer
  2. temperatureThe solution was refluxed for 3 hours
  3. customwith azeotropic removal of water
  4. washThe toluene layer was washed with 5% sodium bicarbonate solution (1500 ml) and water (1000 ml)
  5. dry with materialThe solution was dried over anhydrous sodium sulphate
  6. distillationdistilled

Sources & evidence

ORD record
ord-c2fa7a031d6b4356a94d37b67d8684d1
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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