GB768650A - Vitamin k intermediates - Google Patents

Vitamin k intermediates

Info

Publication number
GB768650A
GB768650A GB36764/54A GB3676454A GB768650A GB 768650 A GB768650 A GB 768650A GB 36764/54 A GB36764/54 A GB 36764/54A GB 3676454 A GB3676454 A GB 3676454A GB 768650 A GB768650 A GB 768650A
Authority
GB
United Kingdom
Prior art keywords
methyl
naphthohydroquinone
phytyl
vitamin
duolite
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
GB36764/54A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB768650A publication Critical patent/GB768650A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises a 1-monocarboxylic acid ester of 2-methyl-3-phytyl-1,4-naphthohydroquinone and the preparation thereof by reacting a 1-monocarboxylic acid ester of 2-methyl-1,4-naphthohydroquinone in an inert solvent with phytol in the presence of a dehydrating agent that is essentially insoluble under the conditions of reaction, is strongly acidic and does not form esters with phytol. Preferably the starting ester contains up to 8 carbon atoms in the acyloxy group. As dehydrating agents there may be used alkali metal bisulphates, e.g. sodium bisulphate or potassium bisulphate, or cation-exchange resins on the hydrogen cycle, e.g. Duolite C-60 or Duolite C-61. The reaction may be effected in the temperature range 65-90 DEG C. in a solvent such as benzene, toluene, dioxan or ethylene glycol dimethyl ether. Treatment of the 1-monocarboxylic ester of 2-methyl-3-phytyl-1,4-naphthohydroquinone with alkali yields 2-methyl - 3 - phytyl - 1,4 - hydroquinone which may be oxidized to Vitamin K1, e.g. with silver oxide. Examples describe the production of the 1-acetate, 1-propionate, 1-butyrate, 1-valerate, 1-caproate, 1-caprylate, 1-phenylacetate, and 1-benzoate of 2-methyl-3-phytyl-1,4-naphthohydroquinone and of Vitamin K1. Specification 768,651 is referred to.
GB36764/54A 1954-01-12 1954-12-20 Vitamin k intermediates Expired GB768650A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US768650XA 1954-01-12 1954-01-12

Publications (1)

Publication Number Publication Date
GB768650A true GB768650A (en) 1957-02-20

Family

ID=22134642

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36764/54A Expired GB768650A (en) 1954-01-12 1954-12-20 Vitamin k intermediates

Country Status (1)

Country Link
GB (1) GB768650A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1160847B (en) * 1958-08-07 1964-01-09 Hoffmann La Roche Process for the production of decals of 2,3-dimethoxy-1,4-benzohydroquinone and -quinone
DE1178843B (en) * 1959-10-09 1964-10-01 Hoffmann La Roche Process for the production of decoctions of 2,3-dimethoxy-5-methyl-1,4-benzohydroquinones and -quinones
DE1178842B (en) * 1958-12-31 1964-10-01 Hoffmann La Roche Process for the production of decoctions of 2, 3-, 2, 5- or 2, 6-dimethyl-1, 4-benzohydroquinones and -quinones

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1160847B (en) * 1958-08-07 1964-01-09 Hoffmann La Roche Process for the production of decals of 2,3-dimethoxy-1,4-benzohydroquinone and -quinone
DE1178842B (en) * 1958-12-31 1964-10-01 Hoffmann La Roche Process for the production of decoctions of 2, 3-, 2, 5- or 2, 6-dimethyl-1, 4-benzohydroquinones and -quinones
DE1178843B (en) * 1959-10-09 1964-10-01 Hoffmann La Roche Process for the production of decoctions of 2,3-dimethoxy-5-methyl-1,4-benzohydroquinones and -quinones

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