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THE STUDY of REACTIONS INVOLVED in the SYNTHESIS of MESCALINE Catherine Q.^Calraucl A. Thesis Subm Itted to the Fa C U Lty of Th

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THE STUDY of REACTIONS INVOLVED in the SYNTHESIS of MESCALINE Catherine Q.^Calraucl A. Thesis Subm Itted to the Fa C U Lty of Th The study of reactions involved in the synthesis of mescaline Item Type text; Thesis-Reproduction (electronic) Authors Gairaud, Catherine Beatrice, 1926- Publisher The University of Arizona. Rights Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. Download date 29/09/2021 20:00:02 Link to Item http://hdl.handle.net/10150/347679 THE STUDY OF REACTIONS INVOLVED IN THE SYNTHESIS OF MESCALINE Catherine Q.^Calraucl A. Thesis submitted to the faculty of the Department of Chemistry in partial fulfillment of the requirements for the degree of MASTER OF SCIENCE in the Graduate College, University of Arizona 1951 Approved •" . ■ - - - : ^ A0m 6%%EDG!#NT \ :::' ' ;y/ ,;::: :' : 'Ihe author. wishes to express her .sinG.ere: appreciation to Doctor Gerald Lappin for: tiis generous and valuable, as sist anc e. "and encourage­ ment throughout the entire course of this work,- " : i i m m • -y ' TABLE- OF GONTBMTS \ ; ' ■■ : ; ' . iv. '■'" : ' ■ ■■ . • PAGE INTRODUCTION . V » , . » A. v » . 1 1 BuIPiijRT^CEiNTAjU •;«•..« » » •. •» • • / »■ • •- .*• « >,,• « «.12- Preparation of <%) -nit r os terrene - «> . .» . , . = 12 Preparation of co -m ethyl-oo-nitrostyrene. „ '•>/„ „ 3,2 i" Preparation of 3, 4, 5-trjjaethaxy - < o -nitrostyrene- , . 13 . Attempted preparation of 3 S ■ k , 5-trimetho2cybenzaldehyde , . 23 ;. Preparation of 3, bs 3-trimethozybenzoyl chloride . > .. 23 : Preparation of 3, 45; S-trimethossybenBanilide. A, ;v 24 Preparation of 3g 4^ S-trijflethosiybenziinid-chloride» „ . , '. 24 . Preparation of 3, k s ~ 5-trimetho2grbenzaldehyde. 25j, 30 Preparation of 4-iiydrb5?y--35 5-dimethosybenzoic acid » i . > « 25 Preparation of 4-hydroxy~3«, 5-dimethosybenzoic acid ' m ethyl e s te r « . • •*. * • • ° »•.*. .* « * •• « » *• ,® » ® « ® @ 26 Preparation of 4-ailylether-3,, 5--diniet:hoxy benzoic acid: ' ‘ m ethyl e s te r . : . » > . , . v. A i . .. , . „ - = „ 26 •Preparation of the sodium salt of l-allyl-pyrogallol-3j,- A ' •' 5-dimethyl ether, . 26 Preparation of l-allyl-pyrogallpl-3<, 4^ 5-trimethyl ether , 26 Preparation' of pyro.gallol-1 ^ 3-dimethylether-2-allylether . A 27 -.'Preparation of I-allylpyrQgalioi-3j, 5-dimethylether . 27 Preparation of l-allylpyrpgallol-3; 4o 5-trimethyiet.ber A: . 27 Preparation of the glycol of l-allylpyrogallol^^ .4y :’ A ; • 5-trimethylether A A • > A « » . , 28 ■ Treatment /of the glycol, with lead hetracetate ... >A: A A A 28 ■ Rearrangement of the double bond of elemicin . ■/ ■ . A .. ; to form isoelemicin® . - . A: ® '» .'29 . ;;02onolysis- 'of is o e le n ic in "» A « ,« . A , A A A, . A A ® A .■ 29 Attempted reductions of- the nitrostyrene. compounds. „ 30 ' DXDCUbDuON o* 9 o e a 1 6 a - o O o a a o. o c o o » ., o oeo.noee-o 32 sm ttiH i, a , . A . o , . A A a »:'aa,A;, V . 41 BIBLIOGRAPHY A . A . „ A > A A ® ® ® . ,,42 : ^ ■ ■ . : ■ - ' - v' - ; : ..■;- •■.■■■ . - ' ' page 1. C0E)I®SAT1C® OF AIDEHlDEljTtfH iETROIierHANE; „ . , . ... 14 I I . HIGHER GOmm#ATIOH PRODWT3 > . «, . .1 5 I I I . .COmEKSATIOH OF ALDEHYDE IIITH MI'TROEl'HAWE.• . > ... ;l6 '•'. IV. CCWAEISOH OF EOE.CTIOH TIME. .. L . 17. V . COHDENSATIOII OF ALD3HIDE 11®. NITROSfETHAME ¥1TH. : : , ; .’AMliONIUM ACE'EiTE AED: GLACiAL ACEf 1C:. AOID, / v . 19 VI . COHDSNS1IION OF AIDEHIDE AED NITROETHMS VelTH- acetaye m i gmoial acetic; acid., . , 2 0 " V II. CONDEHSATIOK OF ALDEHYDE AMD i^MITRCFROPANE vJITH ' ' - - A ■, AMMOMlDIi ACEIATS AED GLiiCIAL ACETIC ACID . A'-.' . :.. ..; . .. 21 'V III. • COMPARISOII OF YIELDS OF SUBSTITDA’ED-aJ.~IITROSTYREHIS./. '. 35 ; . IX. 0OMFAEISON. OF YIELDS OF SUBSTITUTED-a) -H1TROSTYKMES; . 36 5 . COilPARISGl. OF YIELDS OF SUBSTITUTED-®' -'EITROSTYRMES . .... 36 .v;-' --v-V ' . BrmODUGTION ; - ■ , ; Mescaline, one of thef GCnstitnents of the cacti Anhaloniim lewinii, . has been used by liie Ind,ians of the/ 8onthw%i and,(Me%ico; for many years' ■’ in the' form of ’’Mescal buttohs” for their religions rites „ . This: use is due to the physiological actions which - it produces, first described-by ; .I'; / ; r , " " ' i - v;; lewin. in 1894« It is Chiefly characterized ,by visual;hallucinations • which take’the form of fantastic "shapes of various shades and dolors „: -According-to Tayleur Stockings, there are marked sim ilarities between certain mental disorders, and the effects .produced by m escaline.: A per­ son under the influence of mescaline not only has. hallucinations, but also experiences a change in bodily feelings, a disorder in space and time judgment, and a feeling of•depersonalization and detached observa­ tion of -oneself,.- In this way a condition similar to schizophrenia may ■ ■ be artificially produced, leading to a more carefully controlled•Study . ' of this mental disorder. •. : . y - ■3 -..; i i . - "■ : / In a paper by Hey it was pointed out that if a methyl, group -is sub­ stituted into-the position alpha to the amino group, the resulting iso- . propylamine possesses.central nerrous stimulant activity similar to mes-' . calihe. In general,, this property is not shared with the mono-- and :: dimethozyphenylethylamines which show only a pressor effect of varying , degrees t . The physiological properties of these amines’and the effect - of substitution at different positions is discussed in. more detail by : 4 -:v:'Vy: ■; ■ ■. - y ■ - y y,t;,- : Hartung . ■ Thus,-due to the resemblance between the effects produced by : -mescaline and certain mental disorders, interest has grown In the study of the- effects these analogues of mescaline can. produce in the' treatment of clinical mental disorders.' . - .... : ■ 2 . ' Synthetically, mescaline had .been prepared, as early as. 1919 by 5 : ' : ".y; .v V v,;: t " j \': ■ ■■■: - Spath;' '.(Equation I,'p ,3 ), but not a great deal of work was done until b • ' ...V. ' '"'6 \ ' ^""1 \ ; v'1930 when S l o t t a ' and H e lle r ' (E quations I I j I I I , IV, V, p . 4-6).-, in v e s- : ' tigated several other possible methods:for the.preparation of meacaline 7. • and mescaline-lilce compounds» • In 1934 Hahn and^Vassmuth (Equation Vlb, : P>7)> ' by methods previously used by .Maubhner (Equation Via, . p»7), pre­ pared; mescaline .from elemicin, . More recently Behington and M orin-(Eq- nation VII, p,.8) .published an /improved atethod for' the synthesis of mes-. caline, employirig essentially- Spath1s method with the exception that the , 7 nitrostyrene is reduced with lithium aluminum -hydride. ; . 7 -- V ' . ihe original purpose of this work was to prepare■mescaline, .and mes­ caline-like compounds;and their derivatives frbm-a series of substituted . 7 benzaldehydes .condensed -with nitromethane, nitroethahe,- and 1-nitropro- pane= These, compounds were to be reduced to- phenylethylamines and.con- . ' . ■ verted to- various, derivatives for .examination for'physiologi.cal-.activity - by -a cooperating group under Dr, -Li G,- Cla-rk, Fils; institute for the 7 Study of Human Development, Yellow Springs, Ohio*,. However, owing.to - > certain pecularities of the condensation .of substituted benzaldehydes with the nitroalkanes , it/ was decided tb lim it the present investigation mainly to -a study Of -the,factors involved in the condensation of the al~ . ■ : '7;'. ■ 7" 7 7 .V ; i:-/.;. - 77::-7 '-/.77 7 . - 7./\ -/' : V; J 777.-7 -- dehyd.es with the nitroalkanes-,/. .It was hoped -that impr°ved coiidlteions/. .. ' .. for- this, react ion. might be developed, thus, leading to. a better method- - 7 of" synthesis for mescaline;analogs, - - / .. V ' - ' . " ' ' - 'The first, instance that .such condensations. Gould take -place was1 ' ■ ' . -7 7- ,7 ■ ; tv -710; 7;.. .. : 7.-.7 y7; '.7 :. 7 7; . Vv/;7 : . 7 discovered by Priebs in 1883 who showed that7 to -iiitrostyrene could be 7 7 . formed in a $6^ yield. by hOatlhg benzaldehyde and..nitromethaue in the7' -./ . presence of - zinc chloride, in- a. sealed tube at ."ISO0 (Equation- Vlll,- p ,8.).; ; 3 X CH 3 y=\ - _ Crld CHjQ ^ t f COCu P& ^ CH30 / \cho CH3 ° 2 C HjO c h 3 n o 2 A X . NAOH CH3 ° = = X C H 3 9 = \ DUST CH 3 0 ^ yOigCH^QH h =CH N0 3 AC CH3° V j T CH3O CH 3 O c h 3 o C H ,0 CH2 CH^ NH2 C H-.O + CLrC-CHjCL AL CL NH ^ c h 2 c h , n h 2 ^ CH KCAJ CH2 CH2 NH2 / h2 hfeCN 1 2 ^j)chfeCH2BR < U a a — 6 CH3 o CH-,0 9 0 0 H Chb ° ( x z ) CH 0 + ^ > CH 3O -CHCOOK v y coon c h 3 o C H-> O H CH3 O c h 3Q CHoO \ /7 CH2 CH2 COCL^ c h 3 ° < \ y e n ^CH^COOH c h 3o CH3O NH: n 1/ CH3O CHJ/ = = \ CH3 0 ^ y C H 2 CH2 CO N ^, m C B R > CH3 ° \ x CH. CH3O CH3 ° ’ 7 5 Z T a) c h 3o HO, CngscHca.Bi^ _ CH c H g O ^ c h , o HO CHpCHO C H 3 ^ = C H 3 0 CH3° Z /) ch 2 CH;,NH2 < Hg CH3° \ / r * ^ ■ CH3o C H 30 8 ISJE CHd O CHaO3 CH.O CH=CHNO, Ir! AL 1"^.------ > CH30 Z XcH2CH2NHa CH3O CH3O 3 z n i Q c h o + ch ^ 2 0 H^ V ' - ■ . ■ ' ■ . .: .-,- ::'. , V . ' ; 9 - \/ : . 11 ; , - . i''/: , ""; '■ ■■'-;v : ■ ■: :"/,■: ■ > •, ..... Posner found that the ortho-. a,nd meta-nitrdbenaaldehydes also condense v in the presence of zinc, chloridei but that the para-nitro and other sub- - stituted benzaj.dehyd.es dp not condense,- fhe fact: that-the reaction is . ,. .'limited by .the substitutions on the 'benzene ring and: the difficulty o f . r purification of the products has probably been the.reascn .that this nie- ' ■ bhod is hot used to ahy .great: extent. " . ' . ' . : ; ' . • . ' In 1S9C Henry found that aliphatic aldehydes condensed xfith ni- • tromebhane in the presence of alcoholic potassium, hydroxide or potassium - " .; y "i ■ ■ ■' 13 ' ■ / - ; , , ■ . : . - carbonate? and the follpwing year Thiele showed.that aromatic aide- ' , hydes also would, condense in the.
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