BENZOIC ACID, 2,4-DIMETHOXY-5-(1-METHYLETHYL)- synthesis
- Product Name:BENZOIC ACID, 2,4-DIMETHOXY-5-(1-METHYLETHYL)-
- CAS Number:888216-48-6
- Molecular formula:C12H16O4
- Molecular Weight:224.25
913000-28-9
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Yield:888216-48-6 98%
Reaction Conditions:
Stage #1: methyl 5-isopropyl-2,4-dimethoxybenzoatewith water;potassium hydroxide in methanol; for 3 h;Reflux;
Stage #2: with hydrogenchloride;water
Steps:
A5
Aqueous potassium hydroxide (50% w/v, 0.2 ml) was added to a suspension of methyl 5- isopropyl-2,4-dimethoxybenzoate (330 mg, 1.39 mmol) in methanol (5 ml) and water (2 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (10 ml). The organic material was extracted with ethyl acetate (2 x 30 ml) and the combined organic extracts were evaporated in vacuo to afford 5-isopropyl-2,4-dimethoxybenzoic acid (305 mg, 98%) as an off-white solid. 1H NMR (DMSO-de) 12.07 (1 H, br s), 7.57 (1 H, s), 6.64 (1 H, s), 3.90 (3H, s), 3.85 (3H, s), 3.13 (1 H, m), 1.14 (6H, d). MS: [M+H]+ 225.
References:
WO2009/125230,2009,A1 Location in patent:Page/Page column 106
1071151-44-4
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2150-47-2
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