Reacción #351531

Ecuación de reacción

hydrochloric acid

methyl 2,4-dihydroxybenzoate

potassium carbonate

2-ethylhexyl bromide

→

methyl 4-(2-ethylhexyloxy)-2-hydroxybenzoate

Rendimiento 78.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Otrodropwise at room temperature
3. 3
   workup.ADDITIONAfter the dropwise addition
4. 4
   Extracciónextracted with a 150 ml portion and two 50 ml portions of ethyl acetate
5. 5
   ExtracciónThe resulting extract
6. 6
   Lavadowas washed successively with water
7. 7
   Secadoa saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
8. 8
   Concentraciónconcentrated
9. 9
   Otroto obtain a crude product
10. 10
    OtroThe resultant crude product was purified by column chromatography

Procedimiento

To 30 ml of dimethylformamide (DMF) were added 5.00 g (29.9 mmol) of methyl 2,4-dihydroxybenzoate and 4.52 g (32.7 mmol) of potassium carbonate, and 6.32 g (32.7 mmol) of 2-ethylhexyl bromide was added thereto dropwise at room temperature. After the dropwise addition, the mixture was stirred at 80° C. for 5.5 hours. The reaction mixture was added to 200 ml of dilute hydrochloric acid and extracted with a 150 ml portion and two 50 ml portions of ethyl acetate. The resulting extract was washed successively with water and a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated to obtain a crude product. The resultant crude product was purified by column chromatography to obtain 5.89 g (yield: 78%) of methyl 4-(2-ethylhexyloxy)-2-hydroxybenzoate represented by the following chemical formula (hereinafter referred to as compound 1) as a colorless, clear and oily substance. The analytical results of the product are shown below. ##STR22##

Fuente