Chloroform → 4-Hexadecyloxyphenoxyacetic acid methyl ester

HRID 483577Notes

Reaction equation

HRID 483577 reaction equation
[CH2:1]([O:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>CC(C)=O>[CH3:30][O:29][C:27](=[O:28])[CH2:26][O:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 43779374-(Hexadecyloxy)phenol

Product 1

HCID 102507944-Hexadecyloxyphenoxyacetic acid methyl esterYield 89.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 23 g of p-(hexadecyloxy)phenol, 13.35 g of methyl bromoacetate, 10.45 g of potassium carbonate in 200 ml of acetone is refluxed for 24 hours. The mixture is cooled, chloroform added and filtered. The filtrate is evaporated and the residue crystallized from hexane to give 25 g of the desired compound as a gray white solid.

Workup

  1. temperatureis refluxed for 24 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-cf88eb1d66004d619dd334b61383ae1e
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Reaction notes

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