US2030423A - Alkyl resorcinols - Google Patents

Alkyl resorcinols Download PDF

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Publication number
US2030423A
US2030423A US682270A US68227033A US2030423A US 2030423 A US2030423 A US 2030423A US 682270 A US682270 A US 682270A US 68227033 A US68227033 A US 68227033A US 2030423 A US2030423 A US 2030423A
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alkyl
resorcinol
resorcinols
carbon
alkyl resorcinols
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US682270A
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William E Austin
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BANK OF MANHATTAN Co
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BANK OF MANHATTAN Co
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    • 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
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof

Definitions

  • This invention relates to new higher alkyl resorcinols characterized by the fact that the alkyl group is attached to the resorcinol nucleus by a carbon other than an end carbon and contains not less than seven carbon atoms.
  • the compounds may be represented by the general formula C6H3(OH)2(CR1R2R3) in which R1 may be hydrogen or an alkyl and R2 and R3 are alkyl groups, either straight chain or branched, the group (CR1R2R3) containing not less than seven carbon atoms.
  • the compounds within the scope of this invention are the heptyl, the octyl and the nonyl derivatives of resorcinol.
  • the new alkyl resorcinols may be prepared very efficiently, simply and comparatively cheaply by the condensation of resorcinol with an alcohol or alkyl halide having the desired number and arrangement of carbon atoms.
  • the new alkyl resorcinols are characterized by special germicidal and antiseptic properties combined with practical non-toxicity. They may be incorporated in various solutions, jellies, lozenges or other vehicles in proportions ranging up to five parts of the alkyl resorcinol for one thousand parts of the medium, and in special preparations for internal administration they may be used in higher concentrations ranging up to full strength.
  • Secondary octyl resorcinol may be prepared by the process described in the following example: A mixture of g. of resorcinol, 25 g. of secondary octanol (methyl n-hexyl carbinol, CH3CHOHCH2CH2CI-I2CH2CH2CH3), and 10 g. of zinc chloride is heated to C. until water distills off. More of the octanol is added slowly at such rate as to correspond to the water distilling off. The oil which comes off with the waterisconstantly returned to the reaction mixture by means of a water separator. After a total of 80 gr. of the octanol has been added, the reaction is allowed to continue for one hour, after which the temperature is raised to 200 C. when heating is stopped. The resulting oil is washed with water and distilled, the fraction boiling at -210 C.
  • the distillate is a colorless to pale yellow oil.
  • Secondary heptyl resorcinol may be prepared by the process described in the following example: 22 g. resorcinol, 36 g. secondary heptyl bromide (CI-I3CI-I2CH2CHBICH2CH2CH3) and 5 g. anhydrous zinc chloride are mixed and heated while stirring to 130 C. until no further evolution of gas takes place. The mixture is allowed to cool, taken up with toluol, and washed several times with water, then it is distilled in vacuo. The distillate is redistilled and the fraction boiling at 1'75-190 C. (3 mm.) is collected.
  • Secondary heptyl resorcinol having the formula CHOHICHI CHQuH3(QH)3 5.
  • Secondary octyl resorcinol having the formula omomomcmom mula CHzCHzCHzCH:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

Patented Feb. 11, 1936 UNITED STATES ALKYL RESORCINOLS William E. Austin, New York, N. 'Y., assignor to Bank of The Manhattan Company No Drawing. Application July 26, 1933, Serial No. 682,270
6 Claims.
This invention relates to new higher alkyl resorcinols characterized by the fact that the alkyl group is attached to the resorcinol nucleus by a carbon other than an end carbon and contains not less than seven carbon atoms.
The compounds may be represented by the general formula C6H3(OH)2(CR1R2R3) in which R1 may be hydrogen or an alkyl and R2 and R3 are alkyl groups, either straight chain or branched, the group (CR1R2R3) containing not less than seven carbon atoms.
Among the compounds within the scope of this invention are the heptyl, the octyl and the nonyl derivatives of resorcinol.
The usual method for preparing alkyl resorcinols, namely treating resorcinol with a fatty acid, fatty acid chloride or fatty acid anhydride in the presence of a condensing agent, and then reducing the resulting ketone produces only primary alkyl resorcinols. The compounds of the present invention cannot be obtained by this procedure.
The new alkyl resorcinols may be prepared very efficiently, simply and comparatively cheaply by the condensation of resorcinol with an alcohol or alkyl halide having the desired number and arrangement of carbon atoms.
The new alkyl resorcinols are characterized by special germicidal and antiseptic properties combined with practical non-toxicity. They may be incorporated in various solutions, jellies, lozenges or other vehicles in proportions ranging up to five parts of the alkyl resorcinol for one thousand parts of the medium, and in special preparations for internal administration they may be used in higher concentrations ranging up to full strength.
Secondary octyl resorcinol may be prepared by the process described in the following example: A mixture of g. of resorcinol, 25 g. of secondary octanol (methyl n-hexyl carbinol, CH3CHOHCH2CH2CI-I2CH2CH2CH3), and 10 g. of zinc chloride is heated to C. until water distills off. More of the octanol is added slowly at such rate as to correspond to the water distilling off. The oil which comes off with the waterisconstantly returned to the reaction mixture by means of a water separator. After a total of 80 gr. of the octanol has been added, the reaction is allowed to continue for one hour, after which the temperature is raised to 200 C. when heating is stopped. The resulting oil is washed with water and distilled, the fraction boiling at -210 C.
(3 mm.) being collected. The distillate is a colorless to pale yellow oil.
Secondary heptyl resorcinol may be prepared by the process described in the following example: 22 g. resorcinol, 36 g. secondary heptyl bromide (CI-I3CI-I2CH2CHBICH2CH2CH3) and 5 g. anhydrous zinc chloride are mixed and heated while stirring to 130 C. until no further evolution of gas takes place. The mixture is allowed to cool, taken up with toluol, and washed several times with water, then it is distilled in vacuo. The distillate is redistilled and the fraction boiling at 1'75-190 C. (3 mm.) is collected.
It is to be understood that the foregoing emb'odiments are merely illustrative and .by no means limitative of the invention which may assume various-other formsas to the procedures and as to the particular alkyl resorcinols prepared-within the scope of the appended claims.
I claim:
1. Alkyl resorcinols of the general formula CeH3(OH)2(CHR1R2) where H is hydrogen, and R1 and R2 are alkyls, the group (CI-IRaRz) containing not less than seven carbon atoms, and being attached to the resorcinol nucleus by a carbon other than an end carbon.
2. Hep tyl resorcinols in which the alkyl is a secondary heptyl group attached to the resorcinol nucleus by a carbon other than an end carbon.
3. Octyl resorcinols in which the alkyl is a secondary octyl group attached to the resorcinol nucleus by a carbon other than an end carbon.
4. Secondary heptyl resorcinol having the formula CHOHICHI CHQuH3(QH)3 5. Secondary octyl resorcinol having the formula omomomomcmom mula CHzCHzCHzCH:
CH-CQH3(OH)I CHzCHzCHzOHI WILLIAM E. AUSTIN.
US682270A 1933-07-26 1933-07-26 Alkyl resorcinols Expired - Lifetime US2030423A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2439421A (en) * 1944-08-04 1948-04-13 Mathieson Alkali Works Inc Process for the production of dialkylated polyhydric phenols
US2509386A (en) * 1950-05-30 Debenzopyran marihuana-like
US2839570A (en) * 1953-08-12 1958-06-17 Hoffmann La Roche Process for the production of 1-acyloxy-2-methyl-3-phytyl-4-hydroxy naphtalenes
US4093667A (en) * 1977-03-14 1978-06-06 Continental Oil Company Preparation of 4-n-hexylresorcinol
WO2004052814A1 (en) * 2002-12-09 2004-06-24 Unilever Plc Process for the preparation of a cosmetic active

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2509386A (en) * 1950-05-30 Debenzopyran marihuana-like
US2439421A (en) * 1944-08-04 1948-04-13 Mathieson Alkali Works Inc Process for the production of dialkylated polyhydric phenols
US2839570A (en) * 1953-08-12 1958-06-17 Hoffmann La Roche Process for the production of 1-acyloxy-2-methyl-3-phytyl-4-hydroxy naphtalenes
US4093667A (en) * 1977-03-14 1978-06-06 Continental Oil Company Preparation of 4-n-hexylresorcinol
WO2004052814A1 (en) * 2002-12-09 2004-06-24 Unilever Plc Process for the preparation of a cosmetic active

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