Myristyl bromide → [4-(Tetradecyloxy)phenyl]acetic acid methyl ester

HRID 247960Notes

Reaction equation

HRID 247960 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CC(C)=O>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 10316608[4-(Tetradecyloxy)phenyl]acetic acid methyl esterYield 63.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 200 g of methyl 4-hydroxyphenylacetate, 350.4 g of 1-bromotetradecane, 207.9 g of potassium carbonate, 10 g of potassium iodide and 1.5 L of acetone is heated at reflux temperature for 24 hours. The reaction is cooled to room temperature, concentrated in vacuo and the residue is recrystallized from cold hexane to give 276.0 g of the desired product.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 24 hours
  3. concentrationconcentrated in vacuo
  4. customthe residue is recrystallized from cold hexane

Sources & evidence

ORD record
ord-b5c5404327bd4c32abb4ab6dc6a6df55
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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