Water → 2-(2-methoxyethoxy)ethyl bromoacetate

HRID 1651373Notes

Reaction equation

HRID 1651373 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=[O:4].[CH3:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Br:1][CH2:2][C:3]([O:5][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 6227Bromoacetic AcidHCID 8134Diethylene Glycol Monomethyl EtherHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 2213882-(2-methoxyethoxy)ethyl bromoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 13.9 g (0.1 mmol) of bromoacetic acid in 40 ml of toluene was treated with 11.8 ml (0.1 mol) of diethylene glycol monomethyl ether and 0.8 g of p-toluenesulphonic acid monohydrate. The mixture was heated under reflux on a water separator until water no longer separated. The reaction mixture was washed in succession with water, saturated sodium bicarbonate solution and water. The organic phase was dried over sodium sulphate and concentrated. Flash chromatography of the residue on 500 g of silica gel (elution agent methylene chloride/ether 4:1) yielded 2-(2-methoxyethoxy)ethyl bromoacetate as a pale yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. customno longer separated
  3. washThe reaction mixture was washed in succession with water, saturated sodium bicarbonate solution and water
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c55528ca2a94091a48f2aa06cd57644
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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