2,5-Dichlorophenol → HCID 88743094, compound

To a three-necked, 1000 ml flask provided with a mechanical stirrer and a reflux condenser was added 130.4 grams (0.8 mole) 2,5-dichlorophenol (prepared as described in step 1) dissolved in 300 ml absolute, i.e., anhydrous, ethanol. To the phenol solution was added, at ambient temperature, 32.4 grams (0.81 mole) sodium hydroxide dissolved in 300 ml absolute ethanol. The resulting mixture was stirred for 30 minutes and then 133.6 grams (0.8 mole) ethyl bromoacetate was added over a period of 15 minutes. The resulting mixture was stirred for about 30 hours at ambient, i.e., about 23° C., temperature. (A white precipitate, believed to be sodium bromide, was apparent after stirring for about 1 hour.) After completion of stirring the mixture was filtered and the filtrate was concentrated on a rotary evaporator at 55° C., 140 mm Hg and a suspended solids containing liquid was obtained. Both the liquid and the solids were taken-up in 200 ml carbon tetrachloride and transferred to a separatory funnel. The mixture was washed twice with 50 ml portions of 1 N sodium hydroxide solution and once with 50 ml of water. After washing, the organic phase was separated, dried over magnesium sulphate, filtered and the filtrate concentrated on a rotary evaporator at 55° C., 140 mm Hg, a reddish-yellow liquid being obtained. The liquid was taken up in 150 ml of carbon tetrachloride, treated with 2 grams activated charcoal, filtered and the filtrate was concentrated on a rotary evaporator at 55° C., 140 mm Hg. 190 grams of a light yellow liquid corresponding to a 92 percent yield of ethyl-2,5-dichlorophenoxy acetate was thus obtained.

1. customTo a three-necked, 1000 ml flask provided with a mechanical stirrer and a reflux condenser
2. dissolutiondissolved in 300 ml absolute
3. stirringThe resulting mixture was stirred for about 30 hours at ambient, i.e., about 23° C., temperature
4. stirringafter stirring for about 1 hour
5. stirring) After completion of stirring the mixture
6. filtrationwas filtered
7. concentrationthe filtrate was concentrated on a rotary evaporator at 55° C.
8. addition140 mm Hg and a suspended solids containing liquid
9. customwas obtained
10. customtransferred to a separatory funnel
11. washThe mixture was washed twice with 50 ml portions of 1 N sodium hydroxide solution and once with 50 ml of water
12. washAfter washing
13. customthe organic phase was separated
14. dry with materialdried over magnesium sulphate
15. filtrationfiltered
16. concentrationthe filtrate concentrated on a rotary evaporator at 55° C.
17. custom140 mm Hg, a reddish-yellow liquid being obtained
18. additiontreated with 2 grams
19. filtrationfiltered
20. concentrationthe filtrate was concentrated on a rotary evaporator at 55° C.

ORD record

ord-6b01ce67a1314589a11393edc7b742a2

Source dataset

uspto-grants-1982_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04326882