Ethyl 2-hydroxy-6-methylbenzoate

Preparation of 2-Allyloxy-6-methyl-be'zoic acid (Compound 14): Under N2, the mixture of ethyl 2-hydroxy-6-methyl-benzoate (5.00 g, 27.75 mmol), allyl bromide (5.08 g, 3.55 ml, 42.00 mmol) and potassium carbonate (4.42 g, 32.00 mrnol) in dry 2-Butanone (100 ml) was heated to reflux for 48h. After the reaction mixture cooled down to 250C, the suspended inorganic salt was removed by filtration. The concentration of the resulting solution by rotary evaporation yielded pale yellowish syrup, which was then mixed with 2N NaOH (20 ml, 40 mmol) and EtOH (30 ml). After this mixture was stirred for 48h at 800C, ethanol was removed at reduced pressure. After the aqueous solution was acidified by 6N HCl to pH 2 at 50C, the mixture was extracted with Et2O (50 ml x 3). The organic phase was combined and washed with water (10 ml x 2) respectively. The ether extract was dried with anhydrous sodium sulfate and then concentrated to give 2-Al]yloxy-6-methyl-benzoic acid as oil (4.44g, 23.10 mmol). The title compound was then treated with of lM sodium trimethylsilanolate (21.0 ml, 21.0 mmol) to give sodium 2-allyloxy-6-methyl-benzoate (4.65 g) as white powder. 1H-NMR (400 MHz, D2O): 7.06 (m, 1 arom. H); 6.73 (m, 2 arom. H); 5.92 (m, -CH=CH2); 5.29, 5.14 (2 d-like, CH=CH2); 4.47 (d-like, CH2-CH=CH2); 2.10 (s, -CH3). 13C-NMR (100 MHz, D2O): 176.86 (C=O); 153.10; 134.09; 133.61; 131.33; 127.99; 122.84; 117.22; 110.91 ; 69.60; 18.36.

Molecular Weight:180.20
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:180.078644241
Monoisotopic Mass:180.078644241
Topological Polar Surface Area:46.5
Heavy Atom Count:13
Complexity:179
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes