Reaktion #95273

Reaktionsgleichung

1-chloro-3-hexanol

isobutylene

1-iodo-3-hexanol

sulfuric acid

sodium iodide

→

3-(tert-butoxy)-1-iodohexane

Lösungsmittel

methylene chloride

2-butanone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 23.4 g
2. 2
   FiltrationThe cooled solution is filtered
3. 3
   workup.DISTILLATIONDistillation of the residue
4. 4
   Sonstigeaffords 32.9 g
5. 5
   Sonstigegives 27 g
6. 6
   SonstigeChromatography on florisil affords 16 g

Vorschrift

A mixture of 23.4 g. of 1-chloro-3-hexanol [Fourneau, et. al., Bull. Soc. Chem. France, 25, 367 (1919)] in 300 ml. of 2-butanone containing 30 g. of sodium iodide is stirred at the reflux temperature for 18 hours. The cooled solution is filtered and the mother liquor is taken to dryness. Distillation of the residue affords 32.9 g. (84%) of 1-iodo-3-hexanol, b.p. 105° C. (10 mm). Treatment of this material in 500 ml. of methylene chloride, containing 4 ml. of concentrated sulfuric acid, with isobutylene according to the procedure described in Example 492 gives 27 g. of crude material. Chromatography on florisil affords 16 g. of product; λmax. 7.22 and 7.37μ (tert-butyl group).

Quelle