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Chlorobutanol is a tertiary alcohol with various therapeutic uses, including as a bacterostatic preservative and local anesthetic. It is a white crystalline substance with specific solubility properties and can be prepared from acetone and chloroform using alcoholic KOH. The document outlines the preparation procedure and physical properties of Chlorobutanol, including its synthesis and isolation methods.

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4 views7 pages

8483

Chlorobutanol is a tertiary alcohol with various therapeutic uses, including as a bacterostatic preservative and local anesthetic. It is a white crystalline substance with specific solubility properties and can be prepared from acetone and chloroform using alcoholic KOH. The document outlines the preparation procedure and physical properties of Chlorobutanol, including its synthesis and isolation methods.

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Keval
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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University Of Anbar

College Of Pharmacy

Pharmaceutical Organic Chemistry


Fourth grade

Prepared by
A.L. Abdulkareem H. Ayfan

Copyright © mail. [email protected].

1
Chlorobutanol is 1,1,1-trichloro-2-methyl-2-
propanol ( it is a tertiary alcohol)
It has been used in therapeutic for a variety of
purposes:
1-Bacterostatic (used as preservative) in many
injectable, ophthalmic & intranasal
preparations.
2-Sedative-hypnotic in the past.
3-Local anesthetic , in painful I.M injectable ,
topical preparations & as a dental analgesic
Physical properties:
1-White crystalline substance exists in two
forms(anhydrous & hydrated )
2-Characteristic camphor-like odour & taste
3-Slightly soluble in H2O (1/125) & freely soluble in
alcohol (1/1). It is more soluble in boiling H2O but
hydrolysis at such temp. will take place readily.

Therefore recrystallized from H2O-alcohol mixture.


Preparation :
It is prepared from acetone & chloroform in
alcoholic KOH (to speed the reaction)
4-Chloro-1-butanol is obtained simply by leading hydrogen
chloride into boiling tetrahydrofuran until the temperature of the
boiling mixture reaches 103.5-105.5°C (ca. 5 hours). 4-Chloro-1-
butanol is isolated in 54-57% yield by distillation in a vacuum, at 15
mm, much hydrochloric acid being at first evolve. 4-Chloro-1-
butanol 84-85 °C/16 mmHg.
White ppt. is produced, may be due to dissociation of a second
molecules of CHCl3 to give Cl-together with K+ to give potassium
chloride (KCl )
Procedure:
1-Mix 33 ml acetone (25 gm) in dry conical flask
with 7 ml chloroform (10 gm)
2-Cool the mixture
3-Prepare alcoholic KOH ( 1.75 gm KOH / 12.5 ml
alcohol) & put in separatory funnel
4-Add this solution (alc. KOH) drop wise from the
separatory funnel on the previous solution within
a period of 15 min.
5-Filter the ppt. KCl
6-Evaporate the filtrate on H2O bath

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