Acetone → 4-Hexadecyloxyphenoxyacetic acid methyl ester

HRID 1728863Notes

Reaction equation

HRID 1728863 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+].CC(C)=O>C(Cl)(Cl)Cl>[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 180AcetoneHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 43779374-(Hexadecyloxy)phenol

Product 1

HCID 102507944-Hexadecyloxyphenoxyacetic acid methyl esterYield 89.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 23 g of product from Example 84, 13.15 g of methyl bromoacetate, 10.45 g of potassium carbonate and 200 ml of acetone is heated at reflux for 24 hours. The reaction is cooled, chloroform added, filtered and concentrated. The residue is recrystallized from hexane to give 25 g of the desired product as a white solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-a965271ce21d4e12b6d1f6dcdcacd11a
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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