"Cinnamyl AIcohoL-
Five grams of the alcohol were distilled with 33.5 g. of constant-boiling hydrochloric acid (molecular ratio I : 5). The product wds solidified by cooling,filtered, and washed. It wasthenmelted and filtered twice through dry filter paper. A clear oil was obtained
whichmeltedat4-g '. Therecordedmeltingpointwas8-9
23.37% chlorine; the theoretical is 23.2770. The yield of chloride wa9 7970 of the theoretical.
Five grams of the alcohol were distilled with 19.5 g. of hydrobromic acid (molecular ratio I : 3 ) . The product was treated in the manner used to purify the chloride. It melted at 18-23O, and decomposed when boiled.The yield was 93% of the theoretical. The percentage of bromine formed was 40.14; the theoretical percentage is 40.61."

.......source,

THE REACTION BETWEEN ALCOHOLS AND AQUEOUS SOLU- TIONS OF HYDROCHLORIC AND HYDROBROMIC ACIDS.
JAMBSF.Noms,M k LWATTANDRUTHTHOMAS

Did anyone ever work out where Psychokitty got the following procedure (unusually for 'her' there is no reference in the text*, there is an alternative reference which should be chased up)

Psychokitty:

(This appears optional. According to the review, commercial zinc dust worked
just fine when used in proceedure A.)

Commercial zinc dust (16 g., 325 mesh) was activated by stirring for 3-4 minutes
with 100 ml of 2% hydrochloric acid. The zinc was immediately filtered under
suction, washed to neutrality with water, and then washed with 50 ml of ethanol,
100 ml of acetone, and diethyl ether. The resulting powder was dried at 90 deg C
under vacuum (10 minutes) and was used within 10 hours of preparation.

Procedure A:

Cinnamyl alcohol (1.30 mm) was dissolved in 75 ml of dry ether saturated with
hydrogen chloride at 0 deg C. Activated zinc dust (5.0 g; 0.076 mol) was slowly
added to the cooled mixture with vigorous stirring at a rate such that the
temperature maintained below 5 deg C. The reaction was exothermic and
considerable hydrogen evolution occurred. The reaction mixture was stirred for
1 hour at 0 deg C and then filtered. The filtrate was shaken with 500 ml of ice
water and then washed to neutrality with aqueous sodium carbonate. The aqueous
washings were dried over sodium sulfate and evaporated under vacuum.
Chromotography of the residual oil over silica gel (Mallinckrodt, 100 mesh,
25 g) using benzene as eluant afforded 60% yield of allybenzene (4 parts) and
propenylbenzene (1 part).

The above ratios seems a little steep for the average bee with the volume of
solvent too great. A more practical method that is on a preparative scale can be
found in Tetrahedron 27, 5081 (1971).

* Although with a little thought it does "look" like a variant of the Clemmensen Reduction in solvent - of which there is a review floating about - applied to the alcohol. It may not have been chased up previously as it 'looks' odd (clemmensen reduction of an alcohol?), but if HCl chlorinates the alcohol and Zn reductively cleaves that C-Cl bond, then the fucker makes sense

Here soon my friend says he will attempt hcl halogenation followed by zn/AA reduction.  we'll see how it goes.

Ok IF someone (and I'd have to get some glass first) were to try the reaction of casia oil ==> cinnamyl acetate ==> cinnamyl alcohol ==> allylbenzene/propenylbenzene:

(a) what would people expect to find in the flask after the last step? How to extract/purify the product mix from the flask, preferentially one component at a time? I mean, cinnamyl alcohol is a no brainer, any extractive technique to remove excess starting product leaving the alkenes? Or removing the alkenes leaving the starting product?

(b) How to (i) Identify; and (ii) separate the alkenes in order to prove/quantify the outcome?

Anyone want to jump in with suggestions? Building procedures is less than trivial

Im sure there are many ways to do it but I reckon dilute, filter, make basic ,steam distill , add CaCl2 to the distillate and stir for a while, extract,wash with saturated Bisulfite, water washes etc, dry extract , fractionate. Decompose adducts and weigh unreacted starting material, aldehydic impurities etc.
Determine if any hydocinmamy alcohol is formed through boiling point.

As to separating the alkenes, why not simply collect the mixed fraction 160-180c and subject the whole thing to your typical alkaline isomerisation,and then re-distill ? Depends which alkene you are after I suppose. A good column and patience.  Im not the most analytical minded person I know.

Second paragraph!

Ive had another quick look for it but I cant locate it. IIRC  Fittig et` al circa 1878 , used aqueous zinc on cinnamyl alcohol to get a mixture of Alkenes/alcohols..
Im sure this is the first report of it, it is in german though which makes it hard to find for someone as lazy as I am.. Im wondering if this is what PK made a translation of, hence no reference.

WizardX, In this case wouldnt that just saponify the halide back to Alcohol + HX ? Surely it cant be that damn straight forward. Nah, thats how the used to make Cinnamyl alcohol from naturally occurring mixed ester back in the day.

Eish you still had that ref.  Do you remember what the yields were like?

thanks lugh, seems like I was about 40 years off