Myristyl bromide → 3-Methoxy-4-(tetradecyloxy)benzeneacetic acid ethyl ester

HRID 1728846Notes

Reaction equation

HRID 1728846 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH3:14])[CH:7]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])=[C:8]([O:13][CH3:14])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 108965Ethyl homovanillate

Product 1

HCID 537662243-Methoxy-4-(tetradecyloxy)benzeneacetic acid ethyl esterYield 68.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 50 g of 3-methoxy-4-hydroxybenzeneacetic acid ethyl ester, 66.1 g of powdered potassium carbonate, 70.57 g of 1-bromotetradecane and 500 ml of acetone is heated at reflux temperature for 76 hours. The reaction is cooled, filtered and the filtrate concentrated in vacuo. The residue is dissolved in methylene chloride, washed with 2% sodium bicarbonate and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane) to give 66.6 g of the desired product as colorless crystals.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 76 hours
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. dissolutionThe residue is dissolved in methylene chloride
  7. washwashed with 2% sodium bicarbonate and saturated sodium chloride
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0872e694bb704a79b2e21d31f9504a5e
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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