Reaction #54879

Reaction equation

1-bromo-4,4-dimethylpentane

1-chloro-8,8-dimethyl-4-nonanol

1-chloro-8,8-dimethyl-4-nonanone

1-chloro-4-acetoxy-8,8-dimethylnonane

ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoate

ethyl 4-(4-acetyl-8-acetoxy-12,12-dimethyltridecyl)benzoate

amyl bromide

ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxy-12,12-dimethyltridecyl)-benzoate

→

4-(4-acetyl-8-hydroxy-12,12-dimethyltridecyl)benzoic acid

Conditions

Workup

1. 1
   OtherThe synthesis of this compound
2. 2
   OtherSubsequent steps afford in order

Procedure

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.

Source