Ethanol → HCID 15396982, compound

Temperature

-78 °C

A mixture of 2.85 g. (26 mmoles)of 1-methoxy-1, 4-cyclohexadiene and 30 ml. of absolute methanol was treated with ozone (1.25 g., 26 mmoles) at -78°C. The resulting mixture was flushed with nitrogen. The mixture was allowed to come to 0°C and 2.42 g. (39 mmoles) of dimethylsulfide were added and the mixture stirred at this temperature for 80 minutes. After cooling to -78°C, a suspension of 1.47 g/ (39 mmoles) of sodium borohydride in 20 ml. of absolute ethanol was added dropwise. The resulting mixture was allowed to come up to room temperature and then stirred for 80 minutes. The methanol was removed under vacuum to produce 3.3 g. of product (88% of theory). B.p. 60° (0.2 mm., short path distillation).

1. additionA mixture of 2.85 g
2. customThe resulting mixture was flushed with nitrogen
3. customto come to 0°C
4. customto come up to room temperature
5. stirringstirred for 80 minutes
6. customThe methanol was removed under vacuum
7. customto produce 3.3 g
8. distillationB.p. 60° (0.2 mm., short path distillation)

ORD record

ord-6e19713432944623b49ee6db0c463a44

Source dataset

uspto-grants-1976_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03962354