Potassium Carbonate → Methyl 2-(3-tert.-butyl-4-hydroxyphenoxy)-acetate

HRID 637808Notes

Reaction equation

HRID 637808 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:5]1[CH:11]=[C:10]([CH:9]=[CH:8][C:6]=1[OH:7])[O:12][CH2:14][C:15]([O:17][CH3:18])=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16043Tert-ButylhydroquinoneHCID 60984Methyl bromoacetate

Product 1

HCID 20256099Methyl 2-(3-tert.-butyl-4-hydroxyphenoxy)-acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

33.2 g of tert.-butyl hydroquinone, 41.35 g of methyl bromoacetate and 37.3 g of potassium carbonate (anhydrous) are refluxed in 300 ml of acetone under nitrogen for 3 days. The solvent is removed under reduced pressure and 500 ml of ether are added. This ether solution is washed with water, dried with magnesium sulfate and evaporated. The residue is distilled in vacuo. The brown distillate obtained at 138°-140° under 10-3 mm Hg is purified by means of column chromatography. The methyl 2-(3-tert.-butyl-4-hydroxyphenoxy)-acetate thus obtained can be crystallised from hexane. Melting point: 87°-89°.

Workup

  1. customThe solvent is removed under reduced pressure and 500 ml of ether
  2. additionare added
  3. washThis ether solution is washed with water
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. distillationThe residue is distilled in vacuo
  7. customThe brown distillate obtained at 138°-140° under 10-3 mm Hg
  8. customis purified by means of column chromatography

Sources & evidence

ORD record
ord-59c4caf1c49d42f9a6c7c23852e8c227
Source dataset
uspto-grants-1985_12
Patent number
US04558131

Reaction notes

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