A convenient one-step synthesis of 2-hydroxy-1,3,5-benzenetricarbaldehyde

被引：22

作者：

Anderson, AA ^{[1
]}

Goetzen, T ^{[1
]}

Shackelford, SA ^{[1
]}

Tsank, S ^{[1
]}

机构：

[1] Agouron Pharmaceut Inc, Alanex Div, San Diego, CA 92115 USA

来源：

SYNTHETIC COMMUNICATIONS | 2000年 / 30卷 / 17期

关键词：

4-hydroxybenzaldehyde - Acid systems - One step synthesis - Steps procedure;

D O I：

10.1080/00397910008086933

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hexamethylenetetramine/trifluoroacetic acid system was demonstrated to be capable of introducing three aldehyde groups into the phenol molecule. Facile, one-step procedures were developed for the preparation of hitherto difficult to synthesize 2-hydroxy-1,3,5-benzenetricarbaldehyde starting from either phenol or 4-hydroxybenzaldehyde. New pKa measurements showed 2-hydroxy-1,3,5-benzenetricarbaldehyde to be an acid stronger than previously reported.

引用

页码：3227 / 3232

页数：6

共 11 条

[1]

ALLEN CFH, 1963, ORG SYNTH COLL, V4, P866

[2]

Duff J. C., 1934, J CHEM SOC, P1305

[3] A new general method for the preparation of o-hydroxy-aldehydes from phenos and hexamethylenetetramine [J].

Duff, JC .

JOURNAL OF THE CHEMICAL SOCIETY, 1941, :547-550

[4] Reactions between hexamethylenetetramine and phenolic compounds Part I A new method for the preparation of 3-and 5-aldehydosalicylic acids [J].

Duff, JC ;

Bills, EJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1932, :1987-1987

[5]

FERGUSON LN, 1946, CHEM REV, V33, P230

[6]

FORMANEK K, 1982, Patent No. 44260

[7]

HAGIWARA M, 1992, Patent No. 506349

[8]

Huff BE, 1997, HETEROCYCLES, V45, P1363

[9]

KUWAE K, 1993, Patent No. 534608

[10] A PRACTICAL METHOD FOR THE LARGE-SCALE PREPARATION OF [N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)1,2-CYCLOHEXANEDIAMINATO(2-)]MANGANESE(III) CHLORIDE, A HIGHLY ENANTIOSELECTIVE EPOXIDATION CATALYST [J].

LARROW, JF ;

JACOBSEN, EN ;

GAO, Y ;

HONG, YP ;

NIE, XY ;

ZEPP, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1939-1942

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