Citronellal → HCID 13945690, compound

A solution of citronellal dimethyl acetal [55.0 g, 275 mmole, prepared from racemic citronellal, according to the process described by V. R. Mamdapur et al. in Tetrahedron 20, 2601 (1964)] in methanol (550 ml) was treated at -75° with a stream of ozone for 3.5 h (4.5 g of O3 per hour, 328 mmole of O3). The excess of ozone was purged with argon, the solution was allowed to warm to 0° and then treated with a solution of NaBH4 (5.22 g, 137.5 mmole) in MeOH--H2O (1:1, 154 ml). After 2 h, the reaction mixture was concentrated at reduced pressure, then extracted with ether, and the organic phase was washed to neutrality, dried over MgSO4 and concentrated at reduced pressure. 60.2 g of the desired hexanol (ca. 85% pure) were thus obtained and this product was used as such in the next preparation step. An analytical sample, obtained by preparative GLC (gas-liquid chromatography) gave the following data:

1. customThe excess of ozone was purged with argon
2. temperatureto warm to 0°
3. concentrationthe reaction mixture was concentrated at reduced pressure
4. extractionextracted with ether
5. washthe organic phase was washed to neutrality
6. dry with materialdried over MgSO4
7. concentrationconcentrated at reduced pressure

ORD record

ord-7e83474795994eb6a394f7733d0c525f

Source dataset

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05021402