4-(Methylthio)benzeneacetic acid

Cream crystalline powder

10g of 4-bromophenylacetic acid was added to 20 mL of DMF, 20 mL of DMF was added, 5.0 g of sodium methanethiol was added, Copper 0.5g, nitrogen replacement, stirring to increase the reaction temperature to 130 ° C under nitrogen protection, stirring reaction 24 hours, cooling reactionAnd the remainder were the same as in of the present invention, and the yield was 79.3percent.; Taking 4- bromobenzene acetic acid 10g in 100 ml in three-mouth bottle, by adding DMF20mL, adding a thiol sodium 5.0g, adding cuprous bromide 0.1g, after the replacement of nitrogen, to improving the reaction temperature under stirring 130 °C, under the protection of nitrogen stirring for 4 hours, cooling the reaction liquid, by adding 40percent NaOH5mL, stirring 10 minutes. Cooling the reaction liquid, by adding ethyl acetate 25 ml extraction two, by adding ethyl acetate in 50 ml, by adding 10percent dilute sulfuric acid adjusted to pH 2-4, collecting ethyl acetate, ethyl acetate with water 10 ml after washing, distillation of the ethyl acetate to 20 ml left and right, by adding hexane 20 ml, raise the reaction temperature to reflux, after to be solid entirely dissolved, a slow cooling to room temperature, filtered, scaled to obtain yellowish crystalline, to obtain a target product after drying 6.38g, yield 76.1percent.Taking 4- bromobenzene acetic acid 10g in 100 ml in three-mouth bottle, by adding DMF20mL, adding a thiol sodium 5.0g, adding cuprous bromide 0.1g, after the replacement of nitrogen, to improving the reaction temperature under stirring 130 °C, under the protection of nitrogen stirring for 4 hours, cooling the reaction liquid, by adding 40percent NaOH5mL, stirring 10 minutes. Cooling the reaction liquid, by adding ethyl acetate 25 ml extraction two, by adding ethyl acetate in 50 ml, by adding 10percent dilute sulfuric acid adjusted to pH 2-4, collecting ethyl acetate, ethyl acetate with water 10 ml after washing, distillation of the ethyl acetate to 20 ml left and right, by adding hexane 20 ml, raise the reaction temperature to reflux, after to be solid entirely dissolved, a slow cooling to room temperature, filtered, scaled to obtain yellowish crystalline, to obtain a target product after drying 6.38g, yield 76.1percent.General procedure: 2.2 mmol of phthalic anhydride, 2.7 mmol of the corresponding phenylacetic acid and 0.26 mmol of sodium acetate with 5 mL of toluene were adapted in a round bottom flask to a Dean-Stark apparatus. The mixtures were maintained under Nitrogen at 210-245 C, with magnetic stirring, for 9-33 h. After cooling the reaction mixture was treated with ethyl acetate and washed with (sat.) Na2CO3, brine and water, dried over Na2SO4 and concentrated under reduced pressure to give the crude products. Solid products were purified by crystallization and oils by flash chromatography on silica gel. All phthalides were obtained as Z-isomers, configuration confirmed through NOE or ROESY experiments, and yields ranged 40-95%.Example 17 2-[4-(Methylmercapto)phenyl]-1-ethanol 5.5 ml 1 M borane-tetrahydrofuiran complex was slowly added to a solution of 1 g (5.5 mmole) 4-(methylmercapto)phenyl acetic acid in 5 ml tetrahydrofuran at -10 C. The reaction mixture was allowed to reach room temperature and the reaction was followed by TLC. After completion 10 ml methanol was added and the solvents were evaporated. Diethyl ether and 2 M sodium hydroxide was added, the phases were separated, the organic phase was dried, filtered and evaporated in vacuo to give 0.8 g (yield 84.4%) of 2-[4-(methylmercapto)phenyl]-1-ethanol. 1H-NMR (400 MHz; CDCl3): delta 2.46 (s, 3H), 2.77-2.83 (tr, 2H), 3.74-3.82 (qvart, 2H), 7.12-7.17 (m, 2H), 7.20-7.24 (m, 2H). 13C-NMR (100 MHz; CDCl3): delta 16.2, 38.6, 63.5, 127.2, 129.6, 137.7, 136.2.

Molecular Weight:182.24
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:182.04015073
Monoisotopic Mass:182.04015073
Topological Polar Surface Area:62.6
Heavy Atom Count:12
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes