Hydrochloric Acid → 4-Pentyl-3-cyclohexen-1-methanol

A solution of 4-pentyl-3-cyclohexen-l-carboxylic acid (3.4 g) in tetrahydrofurn (THF; 55 ml) was added dropwise to a cold (0° C.) solution of lithium aluminim hydride (1.37 g) in tetrahydrofuran (THF, 55 ml), in a flask equipped with a condenser. The reaction mixture was stirred at room temperature for at least three hours, re-cooled to 0° C., and water (8 ml) was then added dropwise. An additional 55 ml of THF was added, and the reaction mixture stirred for three hours. The reaction mixture was then acidified with 2 M HCl (150 ml), and extracted with a 1:1 (v:v) ethyl acetate:hexane mixture. The combined organic layers were extracted with saturated sodium chloride and dried over sodium sulfate. The solvent was removed in vacuo, and the resultant oil was distilled (92°-95° C. at c.a. 1 mm Hg) to produce 4-pentyl-3-cyclohexen-1-methanol.

1. customequipped with a condenser
2. temperaturere-cooled to 0° C.
3. stirringthe reaction mixture stirred for three hours
4. extractionextracted with a 1:1 (v:v) ethyl acetate
5. extractionThe combined organic layers were extracted with saturated sodium chloride
6. dry with materialdried over sodium sulfate
7. customThe solvent was removed in vacuo
8. distillationthe resultant oil was distilled (92°-95° C. at c.a. 1 mm Hg)

ORD record

ord-022544d684034edfb1e62bc9026382bc

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05271864