Pyridine → 1,1-Dimethoxy-6-iodohexane

81 g (0.5 Mole) of 6,6-dimethoxy-1-hexanal was added to an ice-cooled mixture of 99.3 g (0.52 Mole) of p-toluene-sulfonyl chloride and 72 ml (0.9 Mole) of pyridine at such a rate that the temperature remained below 15°. Stirring was continued for 2 h at 5°-10°, then cold water was added and the mixture was extracted with ether. The organic layer was washed with 5% aq. AcOH, cold 2% NaOH, dried (Na2SO4), and evaporated at 20°. The residue (190 g) was dissolved in 500 ml of acetone, then a solution of 97.5 g (0.65 Mole) of NaI in 500 ml of acetone was added, and the mixture was stirred for 24 h at room temperature. Most of the solvent was removed in vacuo, then ether was added. The mixture was washed with water, dried (Na2SO4), evaporated and distilled to give 124.9 g (92%) of 1,1-dimethoxy-6-iodohexane, b.p. 76°-78°/0.05 Torr.

1. temperaturecooled
2. customremained below 15°
3. extractionthe mixture was extracted with ether
4. washThe organic layer was washed with 5% aq. AcOH, cold 2% NaOH
5. dry with materialdried (Na2SO4)
6. customevaporated at 20°
7. dissolutionThe residue (190 g) was dissolved in 500 ml of acetone
8. stirringthe mixture was stirred for 24 h at room temperature
9. customMost of the solvent was removed in vacuo
10. additionether was added
11. washThe mixture was washed with water
12. dry with materialdried (Na2SO4)
13. customevaporated
14. distillationdistilled

ORDレコード

ord-71cfb0584a2344e1a3dc39a884485640

出典データセット

uspto-grants-1981_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04302607