GB394195A - Process for the manufacture of the glucosides of phenols and of substances containing phenclic hydroxyl groups - Google Patents

Process for the manufacture of the glucosides of phenols and of substances containing phenclic hydroxyl groups

Info

Publication number
GB394195A
GB394195A GB27817/32A GB2781732A GB394195A GB 394195 A GB394195 A GB 394195A GB 27817/32 A GB27817/32 A GB 27817/32A GB 2781732 A GB2781732 A GB 2781732A GB 394195 A GB394195 A GB 394195A
Authority
GB
United Kingdom
Prior art keywords
phenol
saponifying
acetyl
glucoside
condensing
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
Application number
GB27817/32A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of GB394195A publication Critical patent/GB394195A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/203Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

Glucosides of aromatic hydroxy compounds are prepared by condensing the acetates of reducing sugars with aromatic hydroxy compounds and saponifying the resulting acetyl glucosides. The condensation is effected in the presence of an acidic substance and, if desired, of a solvent, whilst the saponification may be effected with alkali or ammonia or catalytically. Examples are given of the preparation of (1) a -phenol-glucoside by saponifying the tetra-acetyl compound obtained from phenol-and a -penta-acetylglucose in the presence of zinc chloride; (2) b -phenol-glucoside, b -(b -naphthol)-glucoside and b -guaiacol-glucoside by saponifying the corresponding tetra-acetyl compounds obtained from the aromatic hydroxy compound and b -penta-acetylglucose in presence of p-toluenesulphonic acid; (3) b -phenolgalacteside by saponifying the tetra-acetyl compound obtained by condensing phenol with a -penta-acetylgalactose with the acid of zinc chloride; (4) b -phenol-gentiobioside by condensing phenol with b -octa-acetylgentiobiose in the presence of p-toluenesulphonic acid and saponifying the hepta-acetyl product; (5) a -phenol-cellobioside by saponification of the hepta-acetyl-a -phenol-cellobioside prepared from phenol and a -octa-acetylcellobiose in the presence of zinc chloride; (6) o-ohenol-zyloside by condensing phenol with b -phenol-xyloside by condensing phenol with b -xylose-tetraacetate in the presence of p-toluenesulphonic acid and saponifying the triacetyl product; (7) b -thymol-glucoside and b -phenol-glucoside by saponifying the tetra-acetyl compounds obtained by condensing thymol and phenol with b -penta-acetylglucose in presence of p-toluenesulphonic acid.
GB27817/32A 1931-10-16 1932-10-06 Process for the manufacture of the glucosides of phenols and of substances containing phenclic hydroxyl groups Expired GB394195A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE394195X 1931-10-16

Publications (1)

Publication Number Publication Date
GB394195A true GB394195A (en) 1933-06-22

Family

ID=6395815

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27817/32A Expired GB394195A (en) 1931-10-16 1932-10-06 Process for the manufacture of the glucosides of phenols and of substances containing phenclic hydroxyl groups

Country Status (1)

Country Link
GB (1) GB394195A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1043321A1 (en) * 1999-03-29 2000-10-11 Nisshin Flour Milling Co., Ltd. Process for the preparation of tetrahydropyran derivatives
CN110343138A (en) * 2018-04-08 2019-10-18 和德化学(苏州)有限公司 Method using solid super-strong acid as catalyst synthesis arbutin

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1043321A1 (en) * 1999-03-29 2000-10-11 Nisshin Flour Milling Co., Ltd. Process for the preparation of tetrahydropyran derivatives
US6339162B1 (en) 1999-03-29 2002-01-15 Nisshin Pharma Inc. Process for the preparation of tetrahydropyran derivatives
CN110343138A (en) * 2018-04-08 2019-10-18 和德化学(苏州)有限公司 Method using solid super-strong acid as catalyst synthesis arbutin

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