4-(1-((Tert-Butyldimethylsilyl)Oxy)-2-Methylpropan-2-Yl)Benzoic Acid synthesis
- Product Name:4-(1-((Tert-Butyldimethylsilyl)Oxy)-2-Methylpropan-2-Yl)Benzoic Acid
- CAS Number:1005786-00-4
- Molecular formula:C17H28O3Si
- Molecular Weight:308.49
![Benzoic acid, 4-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,1-dimethylethyl]-, ethyl ester](/CAS/20210305/GIF/1005785-98-7.gif)
1005785-98-7
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1005786-00-4
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Yield:1005786-00-4 82%
Reaction Conditions:
Stage #1: ethyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)benzoatewith water;potassium hydroxide in tetrahydrofuran;methanol at 70; for 1 h;Inert atmosphere;
Stage #2: with hydrogenchloride in water at 20;Inert atmosphere;
Steps:
2.C
Step C: To a solution of ethyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)benzoate (2C, 1.0 g, 1.0 equivalents) in a 3:1 mixture of THF/MeOH (0.78 M) was added 0.9 M aqueous solution of KOH (2.9 equivalents). The reaction mixture was heated to 70° C. for 1 h. After stirring, the solvents were evaporated, and the residue was acidified with dilute aqueous HCl and then extracted with CH2Cl2. Combined organic layers were dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography (SiO2) to give 2D (82%) as a white solid: 1H NMR (CHLOROFORM-d) δ ppm -0.07 (s, 6H) 0.82 (s, 9H) 1.32 (s, 6H) 3.56 (s, 2H) 7.47 (d, J=8.7 Hz, 2H) 8.01 (d, J=8.7 Hz, 2H).
References:
US2009/318425,2009,A1 Location in patent:Page/Page column 41
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