Hydrochloric Acid → 4-(4-Hydroxybutyl)phenol

Temperature

15 °C

To a solution of 4-(4-methoxyphenyl)butanol (100 g, 0.55 mole) in dichloromethane, cooled to -75° C. in a dry ice-acetone bath, a solution of boron tribromide (278 g; 2.0 mole) was added slowly over one hour. The cooling bath was then removed and the reaction mixture allowed to warm to 15° C. slowly. The reaction was shown to be complete by thin layer chromatography (TLC). The reaction mixture was again cooled in an ice-water bath; 10% sodium hydroxide solution was added until pH of about 9 was obtained. The resulting mixture was then acidified with concentrated HCl to a pH of about 2. The organic layer was separated, the aqueous layer was extracted once with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give 90 g of crude product. The crude product was purified by dry filtration chromatography using 10% ethyl acetate/dichloromethane as eluent giving an 86% yield of pure 4-(4-hydroxyphenyl)butanol. The 1H NMR was consistent with the assigned structure.

1. customThe cooling bath was then removed
2. temperatureThe reaction mixture was again cooled in an ice-water bath
3. addition10% sodium hydroxide solution was added until pH of about 9
4. customwas obtained
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted once with ethyl acetate
7. dry with materialThe combined organic layers were dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto give 90 g of crude product
11. customThe crude product was purified
12. customby dry
13. filtrationfiltration chromatography

ORD record

ord-6e6cf240e6514740b53792b05f00759d

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05108363