US2073995A

US2073995A - Alkyl cresols

Info

Publication number: US2073995A
Application number: US731898A
Authority: US
Inventors: George W Raiziss; Le Roy W Clemence
Original assignee: Abbott Laboratories
Current assignee: Abbott Laboratories
Priority date: 1934-06-22
Filing date: 1934-06-22
Publication date: 1937-03-16
Anticipated expiration: 1954-03-16

Description

haunted Muri lo, 1937 i o H I V UNITED PATENT ALKYL onnsons No Drawing. Application June 22, 1934, 3 3N0. 731398 2 ill/aims. (Cl. 260-454) Our invention relates tola group of compounds the same procedure, substituting the appropriate which have-bactericidal and bacterio'static value, alcohol and cresol, according to the product deand may be classed as alkyl cresols. They are sired.

also of value as intermediates for halogenated All of the compounds disclosed herein are subalkyl cresols which also have bactericidal and bacstantially colorless oils, soluble in organic solvents teriostatic value, which halogenated compounds and in dilute alkalies, and insoluble in water.

are described and claimed in certain of our co- The physical properties I of the compounds pending ppli ations. which we have prepared are as follows:

It is known that the germicidal value of chem- 1o ical compounds is generally greatly reduced"in Maxithe presence of blood serum or whole blood; 5 The Compound B. P. Press. 2Q 1%;? compounds which we have discovered and which tempiorm the subject matter of this application are of high germicidal value in the presence of blood (1) (bmemywuwnmha, 126427, 8 mm 0.970 I o serum and at the same time are of low toxicity, cresol. I o 13 0 W 165 so that our new compounds can be introduced into Q 353m I the human body in relatively high concentrations 3 (l-methyl-butyD-paraass-144 12 mm. 0.970 us without any deleterious eifect to the patient.

Our new compounds which are specifically 4 (2-methyl-butyD-orthol34-l35 10 mm. 0.973 ion-110 described herein, comprise the Z-methyl-butyl, (5) f: 13H, 9mm Mm tertiary amyl, l-methyl butyl, and l-ethyl propyl ores o derivatives of ortho, meta, and para cresols. All (6) ggggtf' 16 165470 of these compounds may be made by 'substan tially the same process as is described in 00- (7) zg l-propyn-onn l34-138 mm. 0.967 W pending application of one of us, Raiziss applica- (8) (1-ethv l-pr py1)-meta- -14 10 m 0-970 tlon Serial No. 643,521, filed November 19, 1932.

9 i-sth iro yn-psralat-143 10 mm. 0.984 150 -Said method is essentially as follows: cresol- 1 V 204 grams of Zinc chlqrlde are dissolved with (10) Tortiai'y-amyl-ortho- 135-137 mm. 0.973 140 heating and mixing in 132 grams of the particular alcohol, depending upon the alkylgroup which (n) 327'"""' 137440 it is desired to introduce into the cresol nucleus, fl v- 10 0-992 say, 2-methyl-butyl alcohol. The temperature is a raised to the appropriate reaction temperature set forth below; in the case of Z-methyl-butyl- The above compounds have the following 35 ortho-cresol this would be 165-170 C. 108 grams I graphic formulas:

of the desired cresol, ortho-cresoi in this case, are then added gradually. After the addition is complete the temperature is maintained until the (1) 0H (2) mixture separates into two layers and is then QH ,QH ,QH ,CH

40 continued for about one hour until a maximum 1 g on 40 separation occurs. The mixture is then cooled and poured into'two liters of water containing a small amount of HQ]. The oilylayer which 's'eparates is then washed with water several times, (l-methylyhr h em l -me hylyl)- and is extracted with three portions of 10 per cmv m 5 cent NaOI-I (about 300 cc. in each portion) The alkaline extract is allowed to stand until there (3) (4) is a clear separation of the insoluble oil. This is removed by extraction with petroleum ether until cnpmomgm the alkaline layer no longer becomes cloudy on CHLCHWIHDH 50 diluting a small sample with water. The alkaline H CH;

(i-methyl-butyD-para-cresoi (2-methyl-butyl)-ortho-cresoi with water and then distilled in vacuo. The desired fraction is collected at the boiling points cm 55 set forth below; in the case of 2-methyl-butyl- CHLOE-(FREE (6) ortho-cresol, the desired product would be 001- on, lected at 134-135 C. at 10 mm. pressure and has (5) 0H E a specific gravity of 0.973. H on;

G0 The VMIOHS other Pr duc s ar ne by (fl-inethyl-butyl)-meta-cresol (Z-methyl-butyi)-para-cresole m cm 5 omomon (l-qn yl-pco yn-ortho-mool.

omomom (l-othyl-propyi) qua-c0001.

OHaOIhOH- 01H OH (l-ethyl-propyi) Tertiary-amyl-ortho'wl.

Tertiary-amyi-meta-cresoi. Tertiary-amyl-pam-cresol.

We claim as our invention: 1. A cresol derivative having the formula: 10

2. As a. germicide, a ethyl-propyl ortho-cresol. 15

- GEORGE W. RAIZISS.

LE ROY W. CLEMENCE.