Water → 8-Hydroxy-7-methoxy-1-octene

A mixture of 45 g of 7,8-dihydroxy-1-octene and 101.2 g of p-anisylchlorodiphenylmethane in 200 ml of pyridine was allowed to stand at 10° C. for 48 hours. The mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide and this solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period. After stirring an additional 13 hours the mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 400 ml of methanol and stirred with 35 g of Amberlyst 15 resin. The solution was filtered and solvent was removed. The residue was purified by chromatography giving 22.6 g of 8-hydroxy-7-methoxy-1-octene as an oil.

1. extractionextracted with ether
2. dry with materialThe ether solution was dried
3. customevaporated
4. dissolutionThe residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide
5. additionthis solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period
6. additionwas poured into water
7. extractionextracted with ether
8. dry with materialThe ether solution was dried
9. customevaporated
10. dissolutionThe residue was dissolved in 400 ml of methanol
11. stirringstirred with 35 g of Amberlyst 15 resin
12. filtrationThe solution was filtered
13. customsolvent was removed
14. customThe residue was purified by chromatography

ORD record

ord-8549d655d2cd44cbb8f801892a895b24

Source dataset

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05411983