GB485266A - Process for the preparation of bisulphite addition compounds of etherified derivatives of pentahydroxy-fuchsone - Google Patents
Process for the preparation of bisulphite addition compounds of etherified derivatives of pentahydroxy-fuchsoneInfo
- Publication number
- GB485266A GB485266A GB2641337A GB2641337A GB485266A GB 485266 A GB485266 A GB 485266A GB 2641337 A GB2641337 A GB 2641337A GB 2641337 A GB2641337 A GB 2641337A GB 485266 A GB485266 A GB 485266A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bisulphite
- guaiacol
- fuchsone
- sodium
- amylnitrite
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Partly or completely etherified derivatives of hexahydroxytriphenylmethanes containing two hydroxy groups in each benzene nucleus are oxidized, and the resulting fuchsones converted into addition compounds with bisulphites. The triphenylmethanes may be prepared by the customary reactions and the oxidation simultaneously effected. Alkyl, halogen and sulpho groups may be present. In examples: (1) 3 : 31 - 311-trimethoxy-4 : 41 : 411-trihydroxytriphenylmethane is treated with amylnitrite and the fuchsone isolated by treatment with absolute alcohol and dry hydrogen chloride; the resulting crystals are washed with sodium acetate solution and water and reacted with aqueous sodium bisulphite to obtain the sodium bisulphite compound of trimethoxydihydroxyfuchsone: trihydroxydimethoxyfuchsone and monomethoxy tetrahydroxyfuchsone may similarly be isolated in the form of their sodium bisulphite compounds; (2) the hydrochloride of 3 : 31-dimethoxy - 311 : 411 - methylenedioxy - 41-hydroxyfuchsone is obtained by oxidizing with amylnitrite the triphenylmethanehydrochloride obtained by condensing piperonal with guaiacol in the presence of hydrochloric acid; the fuchsone is finally treated with aqueous sodium or ammonium bisulphite; (3) 3 : 31 : 311-trimethoxy - 4 : 41 : 411-trihydroxy - 5 - bromtriphenyl methane, obtained from 5-bromvanillin and guaiacol, is oxidized in ethylacetate with amylnitrite and the resulting fuchsone converted into the bisulphite compound; (4) guaiacol is condensed with iodoform, the volatile products removed by distilling on a water bath and the residue dissolved in sodium carbonate; the product obtained by precipitating with acetic acid is extracted with sodium bisulphite solution, decomposed with hydrochloric acid and, after addition of sodium acetate extracted with ethylacetate; by saturating with dry hydrochloric acid, the hydrochloride of trimethoxydihydroxyfuchsone is obtained, which is converted into the bisulphite compound; (5) the calcium salt of m-trimethoxy-p-dihydroxyfuchsone-m-sulphonic acid is obtained either by oxidizing 3 : 31 : 311-trimethoxy-4 : 41 : 411-trihydroxytriphenylmethane-5-sulphonic acid (prepared from guaiacol and 3-methoxy-4-hydroxybenzaldehyde-5-sulphonic acid) or directly by the interaction of amylnitrite, guaiacol and the calcium salt of 3-methoxy-4-hydroxybenzaldehyde-5-sulphonic acid.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2641337A GB485266A (en) | 1937-03-09 | 1937-03-09 | Process for the preparation of bisulphite addition compounds of etherified derivatives of pentahydroxy-fuchsone |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2641337A GB485266A (en) | 1937-03-09 | 1937-03-09 | Process for the preparation of bisulphite addition compounds of etherified derivatives of pentahydroxy-fuchsone |
Publications (1)
Publication Number | Publication Date |
---|---|
GB485266A true GB485266A (en) | 1938-05-17 |
Family
ID=10243257
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2641337A Expired GB485266A (en) | 1937-03-09 | 1937-03-09 | Process for the preparation of bisulphite addition compounds of etherified derivatives of pentahydroxy-fuchsone |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB485266A (en) |
-
1937
- 1937-03-09 GB GB2641337A patent/GB485266A/en not_active Expired
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