Water → HCID 117716545, compound

HRID 1398266Notes

Reaction equation

HRID 1398266 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.[OH2:17]>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:17]

Participants

6

Reactant 3

HCID 962WaterHCID 8117Diethylene GlycolHCID 202106-Bromohexanoic acid

Product 1

HCID 117716545HCID 117716545, compound

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 in a Dean-Stark apparatus with azeotropic removal of water. The solution was cooled to room temperature and the toluene layer was washed with water (600 ml), 5% sodium bicarbonate solution (1500 ml) and water (600 ml). The toluene layer was dried over anhydrous sodium sulphate, filtered 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. washthe toluene layer was washed with water (600 ml), 5% sodium bicarbonate solution (1500 ml) and water (600 ml)
  3. dry with materialThe toluene layer was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. distillationdistilled

Sources & evidence

ORD record
ord-f1a5ebc3f0934cc98ae79b085a718d7d
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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