Ammonia → HCID 20549162, compound

Temperature

100 °C

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.

1. customat -10°
2. extractionThe mixture was extracted with ether
3. dry with materialthe ether extracts dried
4. concentrationconcentrated
5. distillationThe residue (11 g.) was distilled bp. 115°/130°/12 mm Hg
6. additionmixed with formic acid (6.5 g)
7. extractionThe solution was extracted with ether
8. washwashed with NaHCO3 solution
9. dry with materialdried (MgSO4)
10. customThe solvent was removed
11. filtrationThe mixture was filtered
12. extractionextracted with ether
13. extractionextracted with ether
14. customThe ether was removed
15. distillationthe residue was distilled

ORD record

ord-f4a9b93f27ca4989b4f099b9ea8f8892

Source dataset

uspto-grants-1981_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04248859