4-tert-Butyl-2-methoxybenzoic acid synthesis
- Product Name:4-tert-Butyl-2-methoxybenzoic acid
- CAS Number:52328-48-0
- Molecular formula:C12H16O3
- Molecular Weight:208.25
117726-62-2
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52328-48-0
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Yield:52328-48-0 65%
Reaction Conditions:
with lithium hydroxide in 1,4-dioxane at 20 - 60;
Steps:
1A 4-tert-Butyl-2-methoxybenzoic acid
Example 1A
4-tert-Butyl-2-methoxybenzoic acid
500 mg (2.25 mmol) of methyl 4-tert-butyl-2-methoxybenzoate were initially charged in 10 ml of dioxane, and 161.6 mg (24 mmol) of lithium hydroxide were added.
The mixture was stirred at RT overnight and then at 60° C. for 1 h.
After cooling, the reaction mixture was concentrated and taken up in ethyl acetate.
The organic phase was washed with dilute hydrochloric acid, dried over sodium sulphate and concentrated.
This gave 327 mg (65% of theory) of the title compound.
The product is described in Shirley et al J. Organometallic Chemistry, 1974, 69, 327-344.
LC-MS [Method 4]: Rt=2.05 min; MS (ESIpos): m/z=209 (M+H)+
1H-NMR (400 MHz, DMSO-d6): δ [ppm]=1.30 (s, 9H), 3.83 (s, 3H), 7.99-7.04 (m, 1H), 7.04-7.08 (m, 1H), 7.57-7.62 (m, 1H), 12.36 (br. s., 1H)
References:
US2016/318866,2016,A1 Location in patent:Paragraph 0595; 0596; 0597; 0598
124-38-9
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52328-48-0
46 suppliers
$45.00/50mg