Reaktion #64623

Reaktionsgleichung

bromobenzene

Compound 27

bromobenzene

AlCl3

4-methyl valeric acid

4-(4-methylpentyl)-phenylethyne

Compound 26

4-(4-methylpentyl)-phenylethyne

→

Compound 29

4-(1-oxo-4-methyl-pentyl)bromobenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction Scheme 5

Vorschrift

Reaction Scheme 5 discloses a specific synthetic route to 4-(4-methylpentyl)-phenylethyne (Compound 26). In accordance with this scheme, bromobenzene (Compound 27) is reacted under Friedel Crafts conditions (AlCl3) with the acid chloride (Compound 28) prepared in situ from 4-methyl valeric acid, to yield 4-(1-oxo-4-methyl-pentyl)bromobenzene (Compound 29). Compound 29 is reduced under Wolff-Kishner conditions (KOH, NH2NH2) to yield 4-(4-methylpentyl)bromobenzene (Compound 30). The bromobenzene derivative 30 is converted to the ethyne derivative 26 through the intermediate trimethylsilyl ethyne derivative 31 in a manner similar to the conversion described in connection with Reaction Scheme 3. ##STR9##

Quelle