4-Propoxymandelic acid

Adding a mandelic acid derivative (R1=4-propoxy group) 1.0 mmol and p-methylphenol (R2=4-methyl) 0.05 mmol into a 25 mL reaction tube, adding 10 mol% of a nickel triflate catalyst, 160 C The solvent was reacted in vacuo for 12 h. After completion of the reaction, the title compound benzofuranone compound R1=4-propoxy group, R2=4-methyl) was obtained by column chromatography to give a white solid.The yield was 79%.(2) Preparation of the target product:231g of nitrobenzene and 2.9g of sulfuric acid into the reactor, stir, 60 g of condensate and 46.2 g of (1) Preparation of propoxylated almonds:200 g of chloroform and 40 g of p-propoxybenzaldehyde were charged to the reactor, Stir, add 4g of TBAB, continue stirring, 50 at 50 C start dropping uniform liquid caustic soda 160g, The temperature does not exceed 65 C, 8h dropwise addition is complete, start insulation, TLC tracking, insulation 1.5h, the raw material point disappears, the reaction of propoxybenzaldehyde completely, stop holding temperature at this temperature by adding 100g of water and 100g of trichloro Methane, stirred for a while, allowed to stand, layered, and the lower organic layer removed to leave a water layer. Then 60g of chloroform was added to the water layer, stirred for a while, allowed to stand, layered, The lower organic layer was separated and combined with the first separated organic layer to recover the trichloromethane. Then start the water layer hydrochloric acid (30w%) dropsAdd, dropping time of not less than 1h, with pH <3 as the end point. Stirring 1h, filtered to give a pale yellow solid propoxymandelic acid, 50 vacuum drying 24h, dry goods 46.8g, yield 93.6%, stand-by.General procedure: A mixture of mandelic acid(12 mmol), alcohol (1.5 eq) , TsOH (500 mg) and toluene(20mL) wasrefluxed for 2 h. The resultant mixture was diluted with NaHCO3(sat.aq.)(3X10mL) and water( 2X10mL) and dried over Na2SO4.Flash chromatography on silica gel (eluent: ethyl acetate/petroleum ether =6:1) gave the correspondingracemic mandelate ester.General procedure: A mixture of cyanohydrin (14 mmol), 37% HCl (5mL) and dioxane (10 mL) was refluxed for 6 h. The resultant mixture was dilutedwith water (10mL) and extracted with ethyl acetate (3X10mL).The pH value of the organic phase was adjusted to pH=2 with NaHCO3(sat.aq.). The aqueous phase was extracted with ethyl acetate (3X10mL).Thecombined organic phase was washed with brine (3×10 mL) and dried over Na2SO4. Flash chromatographyon silica gel (eluent: ethyl acetate/petroleum ether =2:1) gave the corresponding racemicmandelic acid

Molecular Weight:210.23
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:210.08920892
Monoisotopic Mass:210.08920892
Topological Polar Surface Area:66.8
Heavy Atom Count:15
Complexity:197
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes