GB415715A - The manufacture of therapeutic media - Google Patents

The manufacture of therapeutic media

Info

Publication number
GB415715A
GB415715A GB6132/33A GB613233A GB415715A GB 415715 A GB415715 A GB 415715A GB 6132/33 A GB6132/33 A GB 6132/33A GB 613233 A GB613233 A GB 613233A GB 415715 A GB415715 A GB 415715A
Authority
GB
United Kingdom
Prior art keywords
prepared
octyl
resorcinol
chloro
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB6132/33A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB415715A publication Critical patent/GB415715A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
    • C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/245—Halogenated derivatives monocyclic polyhydroxylic containing halogens bound to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Polyhydroxyhalogenbenzenes, substituted in the nucleus with an alkyl group of 6--12 carbon atoms, are prepared by any of the following processes:--(1) halogenation of a polyhydroxybenzene substituted by an alkyl group of 6--12 carbon atoms (illustrated by examples 1--5 below); halogenation may be effected with p elementary halogen in the presence of a known catalyst, such as iron or aluminium chloride; iodine chloride or a sulphuryl halide may also be used as halogenating agents; halogenation with a sulphuryl halide is preferably effected at a raised temperature in the presence of a solvent, a number of which are specified; (2) condensation of a polyhydroxy-halogenbenzene with an aliphatic alcohol containing 6--12 carbon atoms (illustrated by example 9 below); the reaction is preferably effected in the presence of a condensing agent such as zinc chloride or sulphuric acid; the alcohol may be replaced by an unsaturated aliphatic hydrocarbon containing 6--12 carbon atoms (cf. example 10 below); (3) conversion of a polyhydroxy-halogenbenzene into an acylpolyhydroxy-halogenbenzene containing an aliphatic carboxylic acid radicle of 6--12 carbon atoms, followed by reduction of the acid radicle (cf. examples 6 and 8 below); (4) treatment of an additionally substituted alkylhalogenbenzene or alkylhalogenphenol (the alkyl group containing 6--12 carbon atoms) so as to replace the additional substituent or substituents by a hydroxy group or groups (cf. example 6 below). The products are useful as therapeutic antiparasitic agents. In the examples, (1) 1-n-octyl-5-chloro-2 : 4-resorcinol is prepared by treating 1-n-octyl-2 : 4-resorcinol with sulphuryl chloride; (2) a dichloro1-n-hexyl-2 : 4-resorcinol, and its 1-n-heptyl-and 1-n-octyl-homologs, are prepared by treating the corresponding unchlorinated resorcinols with sulphuryl chloride; (3) a dichloro-1-n-octyl-2 : 4-resorcinol is prepared by treating 1-n-octyl-2 : 4-resorcinol in acetic acid solution with chlorine in the presence of powdered iron; (4) a dibromo-1-n-decyl-2 : 4-resorcinol is prepared by treating 1-n-decyl-2 : 4-resorcinol in carbon tetrachloride with bromine; (5) 1-n-octyl-5-chloro-2 : 4-resorcinol is prepared by treating 1-n-octyl-2 : 4-resorcinol in nitrobenzene solution with sulphuryl chloride; a chlorododecylresorcinol is similarly obtainable; (6) 5-octyl-4-chloro-1 : 2-pyrocatechol is prepared by heating 4-chloro-1 : 2-pyrocatechol with octylic acid in the presence of zinc chloride, and reducing with amalgamated zinc and hydrochloric acid the 5-octylyl-4-chloro-1 : 2-pyrocatechol so obtained; an octyl-4-chloro-1 : 2 : 3-pyrogallol and an octyl-2-bromo-1 : 4-hydroquinone are similarly obtainable; (7) 6-isooctyl-4-chloro-1 : 2-pyrocatechol is prepared by heating 6-isooctyl-4-chloro-2-bromophenol with aqueous caustic soda; (8) a butylhexyl-chlororesorcinol is prepared by condensing a chlororesorcinol with dibutylacetic acid, and reducing with amalgamated zinc and hydrochloric acid the dibutylacetylchloro-resorcinol so obtained; (9) an isohexylchlororesorcinol is prepared by heating a chlororesorcinol with n-heptyl alcohol in the presence of zinc chloride; (10) a heptylchlororesorcinol is prepared by heating a chlororesorcinol with methyldiethylethylene in the presence of zinc chloride. 6-Isooctyl-4-chloro-2-bromophenol, used in example 7, is prepared by heating 4-chlorophenol with n-octyl alcohol in the presence of zinc chloride, and brominating the 6-isooctyl-4-chlorophenol so obtained. Dibutylacetic acid, used in example 8, is prepared by the standard malonic acid synthesis. The Specification, as open to inspection under Sect. 91, indicates that the alkylpolyhydroxyhalogenbenzenes may be prepared from alkylhalogenaminophenols by converting the amino group into a hydroxy group by way of the diazo compound. This subject-matter does not appear in the Specification as accepted.
GB6132/33A 1932-02-29 1933-02-28 The manufacture of therapeutic media Expired GB415715A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE415715X 1932-02-29

Publications (1)

Publication Number Publication Date
GB415715A true GB415715A (en) 1934-08-28

Family

ID=6448507

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6132/33A Expired GB415715A (en) 1932-02-29 1933-02-28 The manufacture of therapeutic media

Country Status (1)

Country Link
GB (1) GB415715A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2579122A (en) * 1949-04-13 1951-12-18 Heyden Chemical Corp Resorcinol recovery process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2579122A (en) * 1949-04-13 1951-12-18 Heyden Chemical Corp Resorcinol recovery process

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