methyl 2-(4-hydroxyphenyl)-2-methylpropanoate synthesis
- Product Name:methyl 2-(4-hydroxyphenyl)-2-methylpropanoate
- CAS Number:123342-40-5
- Molecular formula:C11H14O3
- Molecular Weight:194.2271
67-56-1
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Yield:123342-40-5 95%
Reaction Conditions:
with thionyl chloride at 0 - 20; for 1 - 2 h;Product distribution / selectivity;Heating / reflux;
Steps:
D.5
Step 5 A mixture of a,a-dimethyl 4-hydroxyphenylacetic acid (90.0 g; 499 mmol) and methanol (1 L) was cooled to 0 °C in an ice water bath. To this solution was added thionyl chloride (72.9 mL; 119 g) dropwise with stirring. The resulting solution was heated under reflux for 2 hours. The solution was cooled to room temperature and concentrated in vacuo to afford a solid, which was crystallized from toluene (900 mL) to give methyl 2-(4- hydroxyphenyl) -2-methylpropanoate (92 g, 95%). Alternate procedure: Thionyl chloride (92.4 g; 777 mmol; 200 mol%) was added over 20 minutes to a stirring solution of a,a-dimethyl 4-hydroxyphenylacetic acid (70.0 g; 388 mmmol) in methanol (390 mL). The resulting solution was allowed to stir at ambient temperature for 40 minutes, concentrated, and dried further under high vacuum to give methyl 2-(4- hydroxyphenyl) -2-methylpropanoate (75.3 g, 100%) as a light-brown semi-crystalline solid.
References:
WO2005/121102,2005,A2 Location in patent:Page/Page column 26
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31469-15-5
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59115-08-1
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