Ammonia → HCID 20549162, compound

Participants

Reaction Conditions

Reaction Steps

Magnesium (3.12 g, 0.13 mole), mercuric chloride (0.1 g) and dry tetrahydrofuran (10 ml) were stirred together. Chloromethylethyl ether (12.3 g, 0.13 mole) in tetrahydrofuran (15 ml) was then slowly added at -10° C. 2-Isopropylcycloheptanone (18.5 g, 0.12 mole) in tetrahydrofuran (25 ml) was added slowly keeping the mixture at -10°. This mixture was kept for 15 hours at -10° C. Saturated ammonium chloride solution (100 mls) and dilute ammonia (50 ml) were then added. The mixture was extracted with ether and the ether extracts dried and concentrated. The residue (11 g.) was distilled bp. 115°/130°/12 mm Hg, mixed with formic acid (6.5 g) and heated at 100° C. for 2 hours. The solution was extracted with ether, washed with NaHCO3 solution and dried (MgSO4). The solvent was removed and the residue (11 g), silver oxide (16.2 g, 0.07 mole) and sodium hydroxide (2.8 g. 0.07 mole) in water (150 ml) were stirred at 30° C. for 50 hours. The mixture was filtered and extracted with ether. The aqueous layer was acidified and extracted with ether. The ether was removed and the residue was distilled to give 2-isopropylcycloheptanecarboxylic acid, bp. 120°/0.2 mm.

Provenance & Evidence