Hydrochloric Acid → 3-(4-Chlorophenyl)prop-2-yn-1-ol

A solution of 1-chloro-4-iodobenzene (23.9 g, 100.0 mmol) in dry tetrahydrofuran (100 mL) was degassed and copper(I)iodide (570 mg, 3.0 mmol), tetrakis(triphenylphosphine)palladium (3.4 g, 3.0 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (18.2 g, 120.0 mmol) were added. The reaction solution was degassed again and propargyl alcohol (6.7 g, 120.0 mmol) was added under inert atmosphere at ambient temperature. The reaction mixture was stirred (initially under cooling with ice water) for 24 h, then treated with water (20 mL) and acidified with 2 M hydrochloric acid (20 mL). The organic phase was separated and the aqueous phase was extracted with ether (4×30 mL). The combined organic phases were dried with anhydrous magnesium sulfate and concentrated in vacuo yielding brown solid. The residue was purified by column chromatography (silica gel Fluka 60, chloroform) yielding 3-(4-chlorophenyl)prop-2-yn-1-ol.

1. customThe reaction solution was degassed again
2. customThe organic phase was separated
3. extractionthe aqueous phase was extracted with ether (4×30 mL)
4. dry with materialThe combined organic phases were dried with anhydrous magnesium sulfate
5. concentrationconcentrated in vacuo
6. customyielding brown solid
7. customThe residue was purified by column chromatography (silica gel Fluka 60, chloroform)

ORD record

ord-95de1b6c2d3e43a1b29e43c397fa459d

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362016B2