KR970701684A - Process for manufacturing monoacetal of hydroquinone (PROCESS FOR MAKING MONOACETALS OF HYDROQUINONE) - Google Patents

Process for manufacturing monoacetal of hydroquinone (PROCESS FOR MAKING MONOACETALS OF HYDROQUINONE)

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Publication number
KR970701684A
KR970701684A KR1019960704856A KR19960704856A KR970701684A KR 970701684 A KR970701684 A KR 970701684A KR 1019960704856 A KR1019960704856 A KR 1019960704856A KR 19960704856 A KR19960704856 A KR 19960704856A KR 970701684 A KR970701684 A KR 970701684A
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South Korea
Prior art keywords
mixtures
ether
hydroquinone
group
monoacetal
Prior art date
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KR1019960704856A
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Korean (ko)
Inventor
존 데이비드 카터
잭 리 파슨스
다비드 프레드 스타크스
Original Assignee
레이서 제이코버스 코넬리스
더 프록터 앤드 갬블 캄파니
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Priority claimed from US08/357,849 external-priority patent/US5585525A/en
Application filed by 레이서 제이코버스 코넬리스, 더 프록터 앤드 갬블 캄파니 filed Critical 레이서 제이코버스 코넬리스
Publication of KR970701684A publication Critical patent/KR970701684A/en

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    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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    • C07C43/00—Ethers; Compounds having groups, groups or groups
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    • C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
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    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
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    • A61K8/41—Amines
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    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
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    • C07C41/54—Preparation of compounds having groups by reactions producing groups by addition of compounds to unsaturated carbon-to-carbon bonds
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    • C07—ORGANIC CHEMISTRY
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
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    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

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Abstract

본 발명은 훨씬 높은 순도의 히드로퀴논의 모노 아세탈을 보다 높은 수율로 제조하는 방법에 관한 것이다. 상기 방법은 보호된 히드로퀴논을 예놀 에테르와 반응시켜 보호된 중간체를 형성하는 2-단계 반응을 이용한다. 상기 중간체의 수소화분해 반응에 의해 최종 산물인 모노아세탈 히드로퀴논이 당 분야에 공지된 반응들에 비해 고순도 및 고수율로 형성된다.The present invention relates to a process for producing monoacetals of much higher purity hydroquinone in higher yields. The method utilizes a two-step reaction where the protected hydroquinone is reacted with enol ether to form a protected intermediate. By hydrocracking of the intermediate, the final product, monoacetal hydroquinone, is formed in higher purity and higher yield than the reactions known in the art.

Description

히드로퀴논의 모노아세탈의 제조 방법(PROCESS FOR MAKING MONOACETALS OF HYDROQUINONE)Process for manufacturing monoacetal of hydroquinone (PROCESS FOR MAKING MONOACETALS OF HYDROQUINONE)

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (6)

(a) 산 촉매의 존재하에 히드로퀴논의 모노에테르를 에놀 에테르와 반응시켜 중간체로서 히드로퀴논의 보호된 모노아세탈을 생산하는 단계; 및 (b) 보호기가 선택적으로 분해되도록 금속 촉매의 존재하에 상기 중간체를 수소 전이원과 반응시켜 목적하는 히드로퀴논 모노아세탈을 얻는 단계를 포함하는, 히드로퀴논의 모노아세탈의 제조 방법.(a) reacting monoether of hydroquinone with enol ether in the presence of an acid catalyst to produce a protected monoacetal of hydroquinone as an intermediate; And (b) reacting the intermediate with a hydrogen transition source in the presence of a metal catalyst to selectively decompose the protecting group to obtain the desired hydroquinone monoacetal. 제1항에 있어서, 상기 에테르 보호기가 아릴메틸, 디아릴메틸, 트리아릴메틸, 트리메틸실릴 에테르 및 그의 혼합물로 이루어진 그룹으로부터 선택되고; 바람직하게는 벤질, 지방족 벤질 에테르 및 그의 혼합물로 이루어진 그룹으로부터 선택된 아릴메틸 에테르이고; 더욱 바람직하게는 지방족 벤질 에테르이고; 가장 바람직하게는 모노벤질 에테르인 방법.The compound of claim 1, wherein the ether protecting group is selected from the group consisting of arylmethyl, diarylmethyl, triarylmethyl, trimethylsilyl ether, and mixtures thereof; Preferably arylmethyl ether selected from the group consisting of benzyl, aliphatic benzyl ether and mixtures thereof; More preferably aliphatic benzyl ether; Most preferably monobenzyl ether. 제1항에 있어서, 상기 수소 전이원이 비산성이고 히드라진, 암모늄 포르메이트, 트리알킬암모늄 포르메이트 및 그의 혼합물로 이루어진 그룹으로부터 선택되고, 이때, 수소 전이원 대 중간체 생성물의 몰비는 6:1 내지 1:1이고, 바람직하게는 히드라진 대 중간체 생성물이 4:1 내지 2:1의 몰비인 히드라진인 방법.The method of claim 1 wherein the hydrogen transition source is non acidic and is selected from the group consisting of hydrazine, ammonium formate, trialkylammonium formate and mixtures thereof, wherein the molar ratio of hydrogen transition source to intermediate product is from 6: 1 to 1: 1, preferably hydrazine to intermediate product is hydrazine in a molar ratio of 4: 1 to 2: 1. 제1항에 있어서, 상기 중간체의 형성이 염화 메틸렌, 디에틸에테르, 테트라히드로퓨란, 디옥산 및 그의 혼합물로 이루어진 그룹으로부터 선택된 극성 유기용매, 바람직하게는 염화 메틸렌내에서 수행되는 방법.2. Process according to claim 1, wherein the formation of the intermediate is carried out in a polar organic solvent, preferably methylene chloride, selected from the group consisting of methylene chloride, diethyl ether, tetrahydrofuran, dioxane and mixtures thereof. 제1항에 있어서, 상기 금속 촉매가 팔라듐, 백금, 니켈 및 그의 혼합물로 이루어진 그룹으로부터 선택된 탄서 지지된 금속이고, 이때 지지된 촉매내의 금속의 중량 퍼센트는 2 내지 20%이며; 바람직하게는 탄소상 팔라듐인 방법.The metal catalyst of claim 1, wherein the metal catalyst is a carbonaceous supported metal selected from the group consisting of palladium, platinum, nickel and mixtures thereof, wherein the weight percentage of the metal in the supported catalyst is from 2 to 20%; Preferably palladium on carbon. 제4항에 있어서, 상기 반응이 극성 유기 용매, 바람직하게는 메탄올, 에탄올, 이소프로판올 및 그의 혼합물로 이루어진 그룹으로부터 선택된 히드록시 용매; 가장 바람직하게는 메탄올, 에탄올 및 그의 혼합물내에서 행해지는 방법.The process of claim 4, wherein the reaction is a polar organic solvent, preferably a hydroxy solvent selected from the group consisting of methanol, ethanol, isopropanol and mixtures thereof; Most preferably in methanol, ethanol and mixtures thereof. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019960704856A 1994-03-04 1995-03-03 Process for manufacturing monoacetal of hydroquinone (PROCESS FOR MAKING MONOACETALS OF HYDROQUINONE) KR970701684A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US20657394A 1994-03-04 1994-03-04
US08/206,573 1994-03-04
US08/357,849 1994-12-16
US08/357,849 US5585525A (en) 1994-12-16 1994-12-16 Process for making monoacetals of hydroquinone
PCT/US1995/002738 WO1995023779A2 (en) 1994-03-04 1995-03-03 Process for making monoacetals of hydroquinone

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AU715783B2 (en) * 1994-03-04 2000-02-10 Procter & Gamble Company, The Process for making monoacetals of hydroquinone
KR100453590B1 (en) * 2001-10-17 2004-10-20 주식회사 바이오랜드 Mono carbonylation of Benzene diols
JP4632077B2 (en) * 2002-10-15 2011-02-16 Ｄｉｃ株式会社 Epoxy resin composition, method for producing epoxy resin, novel epoxy resin, and novel phenol resin
WO2006134124A1 (en) * 2005-06-16 2006-12-21 Girindus Ag Synthesis of hydroquinone derivatives
SE535691C2 (en) * 2011-03-08 2012-11-13 Kat2Biz Ab Reduction of C-O bonds via catalytic transfer hydrogenolysis
JP5817614B2 (en) * 2012-03-26 2015-11-18 日本ゼオン株式会社 Method for producing 2,5-dihydroxybenzaldehyde compound

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WO1995023779A3 (en) 1995-09-28
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JPH09509946A (en) 1997-10-07
AU1932295A (en) 1995-09-18
WO1995023778A2 (en) 1995-09-08

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