3,4-Dimethylphenol → HCID 13381509, compound

HRID 1929625Notes

Reaction equation

HRID 1929625 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CC(=O)CC>[CH3:21][O:20][C:18](=[O:19])[CH2:17][O:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 72493,4-DimethylphenolHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 13381509HCID 13381509, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3,4-dimethyl-phenol (5.000 g; 40.928 mmol), potassium carbonate (7.070 g; 51.160 mmol), and methyl bromoacetate (4.70 ml; 51.160 mmol) in butanone (280 ml) was heated at reflux for 4 h. Filtration, concentration to dryness under reduced pressure, and purification by FC (heptane/EA, 4/1) afforded (3,4-dimethyl-phenoxy)-acetic acid methyl ester as a pale yellow oil (7.400 g; 93%). LC-MS: tR=0.92 min.; [M+H]+: no ionisation.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. filtrationFiltration, concentration to dryness
  4. customunder reduced pressure, and purification by FC (heptane/EA, 4/1)

Sources & evidence

ORD record
ord-89769765d3aa4f58a34480477bce017c
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

Loading…