Ammonia → 2-Octyn-1-ol

Under argon atmosphere, a small amount of lithium pieces was added to liquid ammonia (250 ml). The reaction mixture became dark blue in color. A catalytic amount of ferric nitrate nonahydrate was added and the mixture was stirred until the dark blue color disappeared. Lithium pieces (2.75 g, 396 mmol) were further added and the reaction mixture was stirred for one hour. Subsequently, propargyl alcohol (8.16 g, 146 mmol) was added and the mixture was stirred for 30 minutes. Then, n-pentyl bromide (20 g, 132 mmol) was added, and the mixture was stirred for 10 minutes and allowed to stand overnight at room temperature. Water-containing ether (50 ml) and water (200 ml) were added and the resulting mixture was extracted with ether (200 ml, 100 ml, 50 ml×3). The organic layers were combined, washed with water (400 ml) and with brine (400 ml), dried over anhydrous sodium sulfate (50 g) to concentrate. The residue was distilled (b.p.=58°-61° C. at 0.3 mmHg), yielding a colorless oil, 2-octyne-1-ol (9.5758 g, 52% yield). The above described structure of this product was confirmed by the following data.

1. stirringthe reaction mixture was stirred for one hour
2. stirringthe mixture was stirred for 30 minutes
3. stirringthe mixture was stirred for 10 minutes
4. additionwere added
5. extractionthe resulting mixture was extracted with ether (200 ml, 100 ml, 50 ml×3)
6. washwashed with water (400 ml) and with brine (400 ml)
7. dry with materialdried over anhydrous sodium sulfate (50 g)
8. concentrationto concentrate
9. distillationThe residue was distilled (b.p.=58°-61° C. at 0.3 mmHg)

ORD record

ord-9e35f946eba843a68cdfe1d86ebce245

Source dataset

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04880939