1-Bromopentane → 4-(4-Acetyl-8-hydroxy-12,12-dimethyltridecyl)benzoic acid

Participants

Reaction Steps

The synthesis of this compound is carried out as described in Example 1, except that in Step B(1) an equivalent amount of 1-bromo-4,4-dimethylpentane in substituted for amyl bromide. The product of Step B(1) thus becomes 1-chloro-8,8-dimethyl-4-nonanone. Subsequent steps afford in order: Step B(2), 1-chloro-8,8-dimethyl-4-nonanol; Step B(3), 1-chloro-4-acetoxy-8,8-dimethylnonane; Step C, ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoate (unchanged from Example 1); Step D, ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxy-12,12-dimethyltridecyl)-benzoate (by substituting 1-chloro-4-acetoxy-8,8-dimethylnonane for 1-chloro-4-acetoxynonane); Step E, ethyl 4-(4-acetyl-8-acetoxy-12,12-dimethyltridecyl)benzoate; and Step F, 4-(4-acetyl-8-hydroxy-12,12-dimethyltridecyl)benzoic acid, obtained as a viscous yellowish oil.

Provenance & Evidence