Methyl Ethyl Ketone → Methyl 4-(2-bromoethoxy)benzoate

HRID 1579053Notes

Reaction equation

HRID 1579053 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[Br:18][CH:19](Br)[CH3:20].C(C(C)=O)C>C(OCC)(=O)C.CCCCCC>[Br:18][CH2:19][CH2:20][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7456MethylparabenHCID 112011,1-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 1898264Methyl 4-(2-bromoethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 100 g. of methyl p-hydroxybenzoate, 200 g. of anhydrous potassium carbonate, 400 g. of dibromoethane and 1500 ml. of methyl ethyl ketone is refluxed under vigorous stirring for 24 hours, at the end of which time the reaction is essentially complete, as demonstrated by t.l.c. using an ethyl acetate-hexane mixture (60:20) as gradient. The solid is separated by filtration, and the filtrate is evaporated to dryness under vacuo. The oily residue is dissolved in ethyl acetate, washed twice with water, dried over magnesium sulfate and evaporated to dryness under vacuo, to yield methyl 4-(2-bromoethoxy)benzoate.

Workup

  1. additionA mixture of 100 g
  2. customThe solid is separated by filtration
  3. customthe filtrate is evaporated to dryness under vacuo
  4. dissolutionThe oily residue is dissolved in ethyl acetate
  5. washwashed twice with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness under vacuo

Sources & evidence

ORD record
ord-149c22f0a6c3419fa875ce57977d27ac
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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