Acetic Anhydride → 1,6-Octadien-1-ol, 3,7-dimethyl-, 1-acetate, (3S)-

Temperature

120 °C

A 50 mL round-bottom-flask equipped with a condenser was charged with acetic anhydride (6.1 mL, 64.8 mmol), potassium acetate (0.51 g, 5.18 mmol) and triethylamine (4.5 mL, 32.4 mmol). To the stirred mixture was (S)-3,7-dimethyloct-6-enal (5.0 g, 32.4 mmol) slowly. The reaction mixture was heated to 120° C. for 7.5 hours. After cooling to room temperature, the reaction mixture was poured into water (25 mL) and then extracted with toluene (10 mL). The organic layer was washed with saturated aqueous sodium carbonate (25 mL×2) and brine (25 mL). The material was transferred to a 50 ml round-bottom-flask and the separatory funnel was washed with toluene (1 mL). The solution of the title compound in toluene (11 ml) (15.7 g) was used directly for the next step. Mass spectrum (ESI +ve) m/z 187 (M+H+).

1. customA 50 mL round-bottom-flask equipped with a condenser
2. temperatureAfter cooling to room temperature
3. extractionextracted with toluene (10 mL)
4. washThe organic layer was washed with saturated aqueous sodium carbonate (25 mL×2) and brine (25 mL)
5. customThe material was transferred to a 50 ml round-bottom-flask
6. washthe separatory funnel was washed with toluene (1 mL)

ORD record

ord-4ab4bdfa095143c3b27f6b6df3a44c3e

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353063B2