4-Hydroxy-3,5-diMethylbenzoic Acid Methyl Ester synthesis
- Product Name:4-Hydroxy-3,5-diMethylbenzoic Acid Methyl Ester
- CAS Number:34137-14-9
- Molecular formula:C10H12O3
- Molecular Weight:180.2
Yield:34137-14-9 100%
Reaction Conditions:
with thionyl chloride at 20; for 16 h;Cooling with ice;
Steps:
III.a [0107] a) Methyl-3,5-dimethyl-4-hydroxybenzoate, compound 9a
[0108] A solution of 3.5-dimethyl-4-hydroxybenzoic acid (5g, 0.030 mole) in methanol (75 mL) was cooled in an ice-bath and thionyl chloride (8 mL) was added drop wise. The reaction was then warmed to room temperature and stirred for 16 hours. Solid sodium bicarbonate was then added to neutralize the acid and the resulting suspension was concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate (75 mL each). The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. It was then concentrated under reduced pressure to afford a tan powder. Yield = 5.49 g (quantitative). [0109] Compounds 9b (ethyl-3,5-dimethyl-4-hydroxybenzoate, 97% yield) and 9c (isopropyl-3,5-dimethyl-4-hydroxybenzoate, 93% yield ) were prepared similarly.
References:
WO2014/11762,2014,A1 Location in patent:Paragraph 0107; 0108; 0109
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