Toluene → 2-(2-Methoxy-ethoxy)ethyl 8-bromooctanoate

HRID 265368Notes

Reaction equation

HRID 265368 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18]O.C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH3:12])=[O:10]

Participants

6

Reactant 3

HCID 1140TolueneHCID 8134Diethylene Glycol Monomethyl EtherHCID 5482758-Bromooctanoic acid

Product 1

HCID 229164492-(2-Methoxy-ethoxy)ethyl 8-bromooctanoateYield 78.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

8-Bromooctanoic acid (22.3 g), 2-(2-methoxyethoxy)-ethanol (14.08 g) and p-toluenesulphonic acid (0.1 g) were added to toluene (250 ml) and the resulting solution heated at reflux temperature for 16 hours. Ethyl acetate (500 ml) was then added and the solution washed with aqueous K2CO3 solution and water, dried and evaporated. The residual oil was distilled to give 2-(2-methoxyethoxy)-ethyl 8-bromooctanoate (25.5 g), 77%) as a colourless oil, b.p. 126°-128° C./0.08 mm Hg.

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux temperature for 16 hours
  3. washthe solution washed with aqueous K2CO3 solution and water
  4. customdried
  5. customevaporated
  6. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-a8973101963a4b0cbee694a189999e43
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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