2,3-Dimethylphenol → 4-(2,3-Dimethylphenoxy)butanoic acid

2,3-Dimethylphenol (24.5 g, 0.2 mol) was dissolved in 125 ml of anhydrous ethanol. Seventy five (75) ml of 21 wt % sodium ethoxide solution in ethanol (0.2 mol) was added to the solution. The mixture solution was stirred at room temperature for 10 min. Ethyl 4-bromobutyrate (40 g, 0.205 mol) was then added to the solution. The reaction mixture was refluxed at 80° C. for 24 h. The precipitate was filtered of. The filtrate was then mixed with a solution of sodium hydroxide (10 g, 0.25 mol) in 150 ml of water. The mixture was stirred at 70° C. for about 2 hours, and monitored with HPLC. The mixture was diluted with 150 ml of water and acidified to pH 1. Oily precipitate formed immediately. The precipitate was collected by decanting the supernatant and washed with water twice (100 ml×2). The oily precipitate solidified after being kept in water at room temperature overnight.

1. temperatureThe reaction mixture was refluxed at 80° C. for 24 h
2. filtrationThe precipitate was filtered of
3. stirringThe mixture was stirred at 70° C. for about 2 hours
4. customOily precipitate formed immediately
5. customThe precipitate was collected
6. customby decanting the supernatant
7. washwashed with water twice (100 ml×2)
8. waitafter being kept in water at room temperature overnight

ORD record

ord-02f2799bd0824bccadf0a76a277044e8

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895777B2