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

HRID 1376343Notes

Reaction equation

HRID 1376343 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>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

5

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 1

HCID 8857Ethyl AcetateSolvent

Procedure

8-Bromooctanoic acid (22.3 g), 2-(2-methoxyethoxy)-ethanol (14.08 g) and p-toluenesulphouic acid (0.1 g) were added to toluene (250 ml ) and the resulting soution 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 soution 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-61932f2212e046dab0b6b6ec0c9943dc
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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