Editing Synthesis of 3,4-Di(oleyloxy) Benzoic Acid (section)

== 3,4-Di(oleyloxy) Benzoic Acid&nbsp; ==

[[File:Synthesis of 3,4-Di(oleyloxy) Benzoic Acid.png|RTENOTITLE]]

<span style="line-height: 20.8px;">suspend</span>

&nbsp;5.0 g&nbsp;(15.0 mmol) of oleyl bromide, http://www.trc-canada.com/product-detail/?CatNum=O532955, 1g&nbsp;&nbsp; &nbsp;$150.00,&nbsp;10g&nbsp;&nbsp; &nbsp;$1200.00

1.24 g (6.8 mmol) of&nbsp;protocatechuic acid ethyl ester, ([http://www.abcam.com/protocatechuic-acid-ethyl-ester-ab142938.html, 25 http://www.abcam.com/protocatechuic-acid-ethyl-ester-ab142938.html,&nbsp;25] g $115)

2.8 g (20.4 mmol) of&nbsp;potassium carbonate,

and 0.13 g (0.8 mmol) of potassium&nbsp;iodide

in 40 mL of cyclohexanone

stir&nbsp;at 100 °C for 18 h under nitrogen. Because of the&nbsp;light sensitivity of oleyl bromide, the flask should be&nbsp;covered&nbsp;with aluminum foil.

Filter the hot reaction mixture

Remove solvent by&nbsp;a vacuum.

Dissolve the residue&nbsp;in 30 mL of ethanol containing 1.14 g (20&nbsp;mmol) potassium hydroxide and refluxed for 4 h.

Add the hot&nbsp;reaction mixture to 80 mL of water.

Add concentrated hydrochloric acid to pH 1 a<span style="line-height: 20.8px;">cidify&nbsp;</span><span style="line-height: 20.8px;">with&nbsp;</span>the mixture&nbsp;

this will result&nbsp;in&nbsp;the precipitation of a white solid.

Filter the solid &nbsp;and wash&nbsp;several times with water.

<span style="line-height: 20.8px;">Recrystallize t</span>he crude acid&nbsp;from 20 mL of ethanol and dry&nbsp;in a&nbsp;vacuum.&nbsp;

Yield: 3.2 g (72%). mp: 60.5 °C.

Purify by TLC (silica gel)&nbsp;chloroform/methanol (9:1)

cationic lipids can be purified by column chromatography using silica gel 60 (Merck, 70-230 mesh) and dichloromethane (CH2Cl2)/methanol (MeOH) mixtures.
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