Catechol → HCID 13755494, compound

Catechol (110 g) is dissolved in 800 ml isopropanol. A solution of sodium hydroxide (41 g) in 45 ml water is added followed by cyclopropylmethyl chloride (155 g, 70% pure) and potassium iodide (5 g). The reaction mixture is stirred under nitrogen at reflux for 16 hours. The mixture is cooled to room temperature and the solid filtered off and washed with isopropanol. The filtrate is concentrated under reduced pressure, the brown residue dissolved in toluene (600 ml), 3 N hydrochloric acid added to acidify to pH 1 and the organic phase washed consecutively with water (4×100 ml), aqueous sodium bisulfite and water (3×100 ml). The organic layer is dried over anhydrous sodium sulfate, filtered through basic alumina (300 g) to remove any remaining catechol and concentrated under reduced pressure. The residue is distilled in vacuo through a Vigreaux column with reflux distilling head to give 2-(cyclopropylmethoxy)phenol, bp. 66°-68°/0.1 mm.

1. temperatureat reflux for 16 hours
2. filtrationthe solid filtered off
3. washwashed with isopropanol
4. concentrationThe filtrate is concentrated under reduced pressure
5. dissolutionthe brown residue dissolved in toluene (600 ml)
6. addition3 N hydrochloric acid added
7. washthe organic phase washed consecutively with water (4×100 ml), aqueous sodium bisulfite and water (3×100 ml)
8. dry with materialThe organic layer is dried over anhydrous sodium sulfate
9. filtrationfiltered through basic alumina (300 g)
10. customto remove any remaining catechol
11. concentrationconcentrated under reduced pressure
12. distillationThe residue is distilled in vacuo through a Vigreaux column
13. temperaturewith reflux
14. distillationdistilling head

ORD record

ord-e2866957fc4a4bbe96f3e4f668b991a8

Source dataset

uspto-grants-1987_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04634713