Potassium Iodide → Ethyl [4-(Benzyloxy)phenoxy]acetate

HRID 437686Notes

Reaction equation

HRID 437686 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7638MonobenzoneHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 734886Ethyl [4-(Benzyloxy)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 40 g. of 4-benzyloxyphenol, 45.8 g. of ethyl bromoacetate, 40.0 g. of potassium carbonate, 2 g. of potassium iodide and 400 ml. of acetone was heated at reflux for 24 hours. The reaction mixture was filtered and concentrated in vacuo, and the residue was recrystallized from an ether-petroleum ether mixture to give 50 g. of ethyl 4-benzyloxyphonoxyacetate, m.p. 72°-73° C.

Workup

  1. additionA mixture of 40 g
  2. temperatureat reflux for 24 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated in vacuo
  5. customthe residue was recrystallized from an ether-petroleum ether mixture
  6. customto give 50 g

Sources & evidence

ORD record
ord-d29ce17b2e7f4713ba731b4bb8b4a2e5
Source dataset
uspto-grants-1977_06
Patent number
US04031246

Reaction notes

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