Sec- butyl

Reflux a mixture of 68 g. of anhydrous zinc chloride (e.g., sticks), 40 ml. (47 -5 g.) of concentrated hydrochloric acid and 18-5 g. (23 ml.) of sec.-butyl alcohol (b.p. 99-100°) in the apparatus of Fig. 777, 25, 1 for 2 hours. Distil oflF the crude chloride untU the temperature rises to 100°. Separate the upper layer of the distillate, wash it successively with water, 5 per cent, sodium hydroxide solution and water dry with anhydrous calcium chloride. Distil through a short column or from a Claisen flask with fractionating side arm, and collect the fraction of b.p. 67-70° some high boiling point material remains in the flask. Redistil and collect the pure cc. butyl chloride at 67-69°. The yield is 15 g. 

Successful results have been obtained (Renfrew and Chaney, 1946) with ethyl formate methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl and iso-amyl acetat ethyleneglycol diacetate ethyl monochloro- and trichloro-acetates methyl, n-propyl, n-octyl and n-dodecyl propionates ethyl butyrate n-butyl and n-amyl valerates ethyl laurate ethyl lactate ethyl acetoacetate diethyl carbonate dimethyl and diethyl oxalates diethyl malonate diethyl adipate di-n-butyl tartrate ethyl phenylacetate methyl and ethyl benzoates methyl and ethyl salicylates diethyl and di-n-butyl phthalates. The method fails for vinyl acetate, ieri.-butyl acetate, n-octadecyl propionate, ethyl and >i-butyl stearate, phenyl, benzyl- and guaicol-acetate, methyl and ethyl cinnamate, diethyl sulphate and ethyl p-aminobenzoate. 

You see that substrate they were using sec-butyl alcohol" Well to Strike that looks just like MD-P2Pol ... 

So if one were to replace sec-butyl alcohol in the recipe above with an equimolar amount of safrole in the above reaction, Strike will wager that a positive bromination experience will occur. And all this using the very common 48% aq. HBr The oniy difference being that once the reaction mix had cooled, one should do either of two things (1) distill as described except the bromosafrole will be the last thing to come over (not the first), or (2) flood the reaction mix with water to bring the product out of solution after which it can be physically separated by decanting or sep funnel or some such shit. 

The C4H9 alkyl groups may be derived either from the unbranched carbon skele ton of butane or from the branched carbon skeleton of isobutane Those derived from butane are the butyl (n butyl) group and the 1 methylpropyl (sec butyl) group... 

Italicized prefixes such as sec and tert are ignored when alphabetizing except when they are compared with each other tert Butyl precedes isobutyl and sec butyl precedes tert butyl... 

The lUPAC rules permit cer tain common alkyl group names to be used These include n propyl isopropyl n butyl sec butyl isobutyl tert butyl and neopentyl (Section 2 13)... 

The resulting free radicals react with chlorine to give the corresponding alkyl chlorides Butyl radical gives only 1 chlorobutane sec butyl radical gives only 2 chlorobutane... 

Mass Spectrometry Ethers like alcohols lose an alkyl radical from their molecular ion to give an oxygen stabilized cation Thus m/z 73 and m/z 87 are both more abun dant than the molecular ion m the mass spectrum of sec butyl ethyl ether... 

If the a carbon atom of an aldehyde or a ketone is a chnality center its stereo chemical integrity is lost on enolization Enolization of optically active sec butyl phenyl ketone leads to its racemization by way of the achiral enol form... 

Enol form [achiral may be converted to either (R) or (S) sec butyl phenyl ketone]... 

---