00

D. !STRA T! - Fine Organic Synthesis and Natural Products - Practica! works -IV

year of study

Legend:
6 2

1 - Round-bottomedflask (distillate receiver)

2 - Condenser 3 - Round-bottomed f1ask 4- Water bath with electrical' heating. .' and temperaturecontroll . ' 5 - electricrotatlnqmotor :(el1g ine) 6 - sustaining clamps .' 7 - safety clamps 8 - vacuum conection .
4

5
3 7

Fig. 4 - Rote-vepor distillation

-,

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D. /STRA TI - Fine Organic Synthesis and Natural Products - Practicalworks

..:.../Vyear ofstudy

Legend: 1 - Round-bottornedftask 2 - Liebig cond~nser 3 - Distillationhead 4 - Thermorneter 5 -Adapter 6 - Electric heatlhg-source (or burnerg~zehepting) 7 - Waterbath . 8 - Boiling chips

1-H------4

1 8 7 6

water out

water in

Fig. 3: Distillation of Ethyl ethet: (using an electrical heating and a waterbath}

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D. ISTRA TI - Fine Organic Synthesis and Natural Products - Practical works-

IV yearof study

Legend: 1 - Steam generator 2 - Round-bottomedflask 3. -.QistiUationhead 4 - tiebigcondenser 5 - Ber?:eliusflask 6 - Bun:enburner 7-CI~rnps 8 - Tripo.Qe 9 -Stand 10 -Safety glass tuoe

Fig. 1 - Steam distillation procedure for

extrection ()fLimonen~

Legend: 1- Separatory funnel 2 - Ground-glass stopper 3 - Ground-glass stopcock 4 - Berzelius f1ask(beaker) A - Upper layer (low density) B - Lower layer (high density)

A ---1

<,
-+---3

-+---:,,~-4

Fig.2 - Extraction of Limonene with ethyl ether

D. ISTRA TI- Fine Organic Synthesis and Natural Products - Practical works ..../Vyearofstudy

Extraction of EUGENOLE from cloves

Chemical Structure:

HOyCHZ-CH"CH2

H3CO

Eugenole (2-metoxy-4-alyl phenol)

Procedure: In a 500 mL one-necked round bottomed-flask,eqt4ippedwitha steam distillation apparatus (Fig. 1), introduce 30g of pounded cloves.clndt50mLof hot water. Disttll until the obtained distillatebecomesclear. Extract the aqueous layer with three portions of 15-20 mL methylene chloride (see Note), dry the united organic layer withmcagnesiurJlsulfate arid then distill the solvent using a classlc apparatus (Fig. 3}or a rata-vapor .one (Fig. 4). The product could be identified by its 1H-NMR, IRandMassSpectrum.

Note The denslty of the methylene chlorideis 1.2 g/cm3

D. ISTRA TI - Fine Organic Synthesis and Natural Products - Precticelworks-

.

IV yeer ofstudy
.

Extraction of LIMONENE from Orc:ri1~gePeel

Chemical Structure:

Limonene

Procedure: In a 500 ml one-necked round bottorned-flask, equlppedwith.a stearn distillation apparatus (Fig. 1), introduce 300 9 of oranqe .peeL(from3-4 oranges), cut in smallslices (-1cm) and 100mL of hot water., After distill 2,"300ml of the distillate becorne opaqu~,soft-y~Uow, with a characteristic srnell (as orange and lemon). . ... ' Extract the distillatein three portionswith 20-25 ml,: otet~yrether {Fig. 2) and, after drying the organic layers (upperlayer)with,fn9gnE!}siUrn'sulf~~e, distill the solvent using the .classic apparatus (see Note ).(F'.ig .. 3fo[ using the rata-vapor apparatus (Fig.4). . '., . ". Anorange-yelloWoil of Limonene will be obtained._ .. The product could be identifiedbyits 1H-NMR, IRand,Mas$Sp~(;trurn.

Note, Thedistillation of ethylether must be done witha water bath, provided with electrical heating, withoutdirect flame!

1.

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SAPo~tFICf\TION OF FAT.SOAP
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:~~CEDURE
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.. .Place? g of lardor any fatty oil), 3 g potassiurn hydroxideand 40. nlL alel)qol in' a 250- mlrround-bottomed flask. Attach-a reflux . COrldelser~:ai1d boil thereaction '.'ta~e:;f()rabouL 30 min. The . reaetion isoomplete whenno glesof oil are present when .a few . .... drop of the rnixture are mi~e~ ith .a little water.Distil the reaction ~, , 'ini~tup,~and reeover the alcoliol 'and dissolve the residue in 75 mL of . .'hQt:watcr:, 0"". ' . ", .' .
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Carry out theJ~.oltoW1ngexperim~9tswjJh th&lesulting solution:

":.. .' ': . - .. ::-" -. .:...... .'. '. .~"'~. -.-'--.'.~<--\ " .""-:::."' .

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a, '. saturated solution of Qdiurn,-~chl()I:i;.~i{t~rJhe precipitate. of soap

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i)Too 25 ",PlL,ofthe solution ajJd.!sJOwly,andl.!pderstirri~g

'.'andwash it with a litt(esaturMed,odiUm 'chloride solution.and spread .it onawatch.glass ~0't1ry;' "
o "< ~ -,

i)AcIGify

ihe remaindet

6f .the solution.with

'dilute sulphuric

;.

add,c()ol, fllter and wash witha Httle~water.-Neutralise the filtrate '.' "vithsodi'um carbonate solutionandevaporate, under vacuum, a .waicr, bath in '8 Iarge evaporatingdish .:"~~ Extract theresidue with l5roL of absolutealcohol and filter the alcoholicsolution. Evaporate the alcoholicextract 'on a .'waten . 'batrl.~ _ he viS'eous residue consists of crude glycerol. It .may~~j~' _T identl~:;",; by conversion into tribenzoate. ' .

on

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. .....,;~.

, .!\f.~

. ..Gly'c~rol .trlbenzoate
., I -'

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Place. in a.testtube or smallflask 1.3 g of glyccro! and30:mL '" 'NaOHsolution '1Q%. Aeld>gradually, \vithsimultati~~s:b.aking,t.~ g benzoyl chloride. Stop.the shakeand.gllew.the teactiort'mixture to standrDecant 'the solution fromthe pasty soltd'andw~li the'latter with coid water by decantation.
o. ' :'

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. . ..: Recrystallizetheselidtribenzoate from petr(jletfn~~er.(p~p. 40~ .60"C)~Thepure compound meltsat 760C."

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