Resorcinol → 3-Phenoxyphenol

To a stirred solution of 49.5 g (0.45 mol) of resorcinol in 75 ml dry pyridine under nitrogen atmosphere, 16.2 g (0.3 mol) of Sodium methoxide was added. Heating started and methanol fractionally distilled off over a period of 0.5 hr. Bromobenzene, 142 g (0.9 mole) was run in to the reaction mixture followed by 2.2 g, of Cuprous chloride. Reaction mixture heated under reflux for 3–4 hr, pyridine distilled off while the pot temperature rose to 150° C. The residue was poured into 50 ml conc. HCl in 120 ml water and stirred. Organic material extracted in 200 ml benzene followed by washing with 25 ml of 20% HCl. Organic layer extracted with 100 ml of 10% NaOH solution followed by a second extraction With 20 ml of 10% NaOH. The combined aqueous extracts were acidified with, HClconc, liberated m-phenoxy phenol was extracted into benzene (300 ml). From the organic layer benzene was removed by distillation. Crude product purified by filtration over a column of silica.

1. temperatureHeating
2. distillationmethanol fractionally distilled off over a period of 0.5 hr
3. customReaction mixture
4. temperatureheated
5. temperatureunder reflux for 3–4 hr
6. distillationpyridine distilled off while the pot temperature
7. customrose to 150° C
8. additionThe residue was poured into 50 ml conc. HCl in 120 ml water
9. extractionOrganic material extracted in 200 ml benzene
10. washby washing with 25 ml of 20% HCl
11. extractionOrganic layer extracted with 100 ml of 10% NaOH solution
12. extractionfollowed by a second extraction With 20 ml of 10% NaOH
13. extractionwas extracted into benzene (300 ml)
14. customFrom the organic layer benzene was removed by distillation
15. filtrationCrude product purified by filtration over a column of silica

ORD record

ord-25da70fe8a4948b99b2a6ad48198f1d9

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105577B2