Phenol → Benzene, 1-(3-chloropropoxy)-4-(methylthio)-

A solution of 4-(methylthio)phenol (10.0 g, 0.071 mole) in 150 ml. of 1,2-dimethoxyethane is added to a slurry of a 57% dispersion of sodium hydride (3.0 g., 0.071 mole) in mineral oil (previously washed with hexane to remove the mineral oil) in 100 ml. of 1,2-dimethoxyethane. After the initial reaction is complete, 1-bromo-3-chloropropane (12.63 g., 0.08 mole) is added in one portion. The resulting mixture is stirred and refluxed for a period of 68 hrs., cooled and then concentrated under reduced pressure. Residual material (oil) is dissolved in ether and washed with water. The ether solution (after drying over magnesium sulfate) is concentrated under reduced pressure to provide 14.6 g. of an oil containing approximately 25% starting phenol according to NMR spectra. Distillation of the oil under reduced pressure affords, after a forerun of 4-(methylmercapto)phenol, 5.0 g. (32% yield) of 1-chloro-3-[4-(methylthio)phenoxy]propane, b.p. 150°-152° C. at 27 mm Hg.

1. washpreviously washed with hexane
2. customto remove the mineral oil) in 100 ml
3. customAfter the initial reaction
4. temperaturerefluxed for a period of 68 hrs
5. temperature, cooled
6. concentrationconcentrated under reduced pressure
7. dissolutionResidual material (oil) is dissolved in ether
8. washwashed with water
9. concentrationThe ether solution (after drying over magnesium sulfate) is concentrated under reduced pressure
10. customto provide 14.6 g
11. additionof an oil containing approximately 25%
12. distillationDistillation of the oil under reduced pressure
13. customaffords

ORDレコード

ord-ef82afb4fb2e42d4ba1847aa4f491733

出典データセット

uspto-grants-1979_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04147805