Benzoic acid, 2,6-dihydroxy-, methyl ester

General procedure: Thionyl chloride (1.16 g, 1.5 equiv) was added drop-wise to a solution of acid (1.0 g, 1.0 equiv) in the corresponding alcohol (15 ml) at 0&d eg;C. The solution was refluxed under a nitrogen atmosphere until all starting material was consumed (TLC monitoring). Then the solvent was removed under vacuo and the residue was purified by silica gel column chromatography eluting with ethyl acetate/n-hexane to afford the corresponding carboxylic esters.#10;Add 1.54 g (0.01 mol) of 2, 6-dihydroxybenzoic acid to a 50 mL one-necked flask and add 6 mL (1.48 mol).Water methanol, 0.35 mL of concentrated sulfuric acid, refluxed for 5 h, and methanol was removed under reduced pressure. Add 20mL water, stir well, suction filtration, drying at 40 ° CThe filter cake was recrystallized from cyclohexane to obtain 0.73 g of white needle crystals, yield 43.5percent.a) Step A: To a solution of ethyl 4-((acetyloxy)methyl)-5-{3-((1E)-3-hydroxypr- op-1-enyl)phenyl}isoxazole-3-carboxylate (960 mg, 2.78 mmol) in THF (14 mL) was added methyl dihydroxybenzoate (934 mg, 5.57 mmol) and PPh 3 (1.46 g, 5.57 mmol). After purging the vessel with N 2, diethyazodicarboxylate (968 mg, 5.57 mmol) was added. The mixture was stirred for 16 hours, concentrated under vacuo and the residue purified by column chromatography (0-40% ethyl acetate in hexanes) to provide the titled compound (590 mg, 43%).To a THF (1 mL) solution of compound from Example 21D (150 mg, 0.52 mmol), The 2-(4-amino-butoxy)-6-hydroxy- benzoic acid methyl ester was prepared by taking a solution of To a solution of methyl 2, 6-dihydroxybenzoate (1.0 g, 5.95 mmol) and 4-(Boc-amino)-1- butanol (1.1 ml_, 5.95 mmol) in 60 mL of THF is added PPh3 (1.7 g, 6.5 mmol) and DEAD (2.97 mL, 6.5 mmol). The solution is stirred at RT for 18 h then the solvent is removed under reduced pressure. The residue is purified by flash chromatography using a gradient of hexane /EtOAc (5:1 to 2:1) to give the product as a colorless liquid.

Molecular Weight:168.15
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:168.04225873
Monoisotopic Mass:168.04225873
Topological Polar Surface Area:66.8
Heavy Atom Count:12
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes