Hydrochloric Acid → 3,5-Dimethylhex-3-en-2-one

Under an atmosphere of N2, a 1.6 M solution of MeLi in Et2O (500 ml, 800 mmol) was added during 105 min. dropwise with stirring between 0-10° C. to a solution of 2,4-dimethylpent-2-enoic acid (41.0 g, 320 mmol) in Et2O (1.6 L). The reaction mixture was heated to reflux for 1 h, and then between 5-15° C. 5 N HCl (200 ml) was added dropwise. The organic layer was separated, the aqueous one extracted with Et2O (200 ml). The combined organic solutions were washed with water (200 ml) and brine (100 ml), dried (Na2SO4) and concentrated in a rotary evaporator to afford crude 3,5-dimethylhex-3-en-2-one, which was taken up in Et2O (160 ml). Under N2 at room temp., this solution was added dropwise with stirring to a suspension of LAH (3.34 g, 880 mmol) in Et2O (320 ml) during 1 h. The reaction mixture was refluxed for 2 h, and then quenched between 0-5° C. by addition of water (10 ml) and brine (20 ml). The organic layer was separated and the aqueous one extracted with Et2O (100 ml). The combined ethereal extracts were washed with water (100 ml) and brine (50 ml), dried (Na2SO4), and concentrated under reduced pressure. Silica-gel FC (pentane/Et2O, 4:1, Rf=0.40) of the resulting residue provided 34.7 g (85% over 2 steps) of 3,5-dimethylhex-3-en-2-ol.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 1 h
3. custombetween 5-15° C
4. customThe organic layer was separated
5. extractionthe aqueous one extracted with Et2O (200 ml)
6. washThe combined organic solutions were washed with water (200 ml) and brine (100 ml)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in a rotary evaporator

ORD record

ord-189d4ee55b1c4ab68461a48e798ad58e

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07384906B2