WO1995023779A3 - Process for making monoacetals of hydroquinone - Google Patents

Process for making monoacetals of hydroquinone Download PDF

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Publication number
WO1995023779A3
WO1995023779A3 PCT/US1995/002738 US9502738W WO9523779A3 WO 1995023779 A3 WO1995023779 A3 WO 1995023779A3 US 9502738 W US9502738 W US 9502738W WO 9523779 A3 WO9523779 A3 WO 9523779A3
Authority
WO
WIPO (PCT)
Prior art keywords
hydroquinone
monoacetals
yields
making
purity
Prior art date
Application number
PCT/US1995/002738
Other languages
French (fr)
Other versions
WO1995023779A2 (en
Inventor
John David Carter
Jack Lee Parsons
David Fred Starks
Original Assignee
Procter & Gamble
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
Priority claimed from US08/357,849 external-priority patent/US5585525A/en
Application filed by Procter & Gamble filed Critical Procter & Gamble
Priority to JP7523070A priority Critical patent/JPH09509946A/en
Priority to KR1019960704856A priority patent/KR970701684A/en
Priority to AU19395/95A priority patent/AU1939595A/en
Priority to EP95912054A priority patent/EP0748306A1/en
Priority to CA002184252A priority patent/CA2184252C/en
Priority to MXPA/A/1996/003877A priority patent/MXPA96003877A/en
Publication of WO1995023779A2 publication Critical patent/WO1995023779A2/en
Publication of WO1995023779A3 publication Critical patent/WO1995023779A3/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/30Compounds having groups
    • C07C43/315Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498Cosmetics 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/347Phenols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4986Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55Phosphorus compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier 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
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/02Preparations for care of the skin for chemically bleaching or whitening the skin
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48Preparation of compounds having groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48Preparation of compounds having groups
    • C07C41/50Preparation of compounds having groups by reactions producing groups
    • C07C41/54Preparation of compounds having groups by reactions producing groups by addition of compounds to unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04Heterocyclic 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
    • C07D307/18Heterocyclic 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
    • C07D307/20Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02Heterocyclic 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
    • C07D309/08Heterocyclic 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
    • C07D309/10Oxygen atoms
    • C07D309/12Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention is for a process for preparing monoacetals of hydroquinone wherein said process provides for higher yields of greater purity. Said process utilizes a two-step reaction wherein a protected hydroquinone is reacted with an enol ether to form a protected intermediate. Upon hydrogenolysis of said intermediate, a final product, monoacetal hydroquinone, is formed having higher degree of purity and in greater yields than the yields attributed to reactions known in the art.
PCT/US1995/002738 1994-03-04 1995-03-03 Process for making monoacetals of hydroquinone WO1995023779A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP7523070A JPH09509946A (en) 1994-03-04 1995-03-03 Method for producing monoacetal of hydroquinone
KR1019960704856A KR970701684A (en) 1994-03-04 1995-03-03 Process for manufacturing monoacetal of hydroquinone (PROCESS FOR MAKING MONOACETALS OF HYDROQUINONE)
AU19395/95A AU1939595A (en) 1994-03-04 1995-03-03 Process for making monoacetals of hydroquinone
EP95912054A EP0748306A1 (en) 1994-03-04 1995-03-03 Process for making monoacetals of hydroquinone
CA002184252A CA2184252C (en) 1994-03-04 1995-03-03 Process for making monoacetals of hydroquinone
MXPA/A/1996/003877A MXPA96003877A (en) 1994-03-04 1995-03-03 Procedure for developing monoacetals dehydroquin

Applications Claiming Priority (4)

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

Publications (2)

Publication Number Publication Date
WO1995023779A2 WO1995023779A2 (en) 1995-09-08
WO1995023779A3 true WO1995023779A3 (en) 1995-09-28

Family

ID=26901478

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/US1995/002382 WO1995023778A2 (en) 1994-03-04 1995-02-27 Process for making monoacetals of hydroquinone
PCT/US1995/002738 WO1995023779A2 (en) 1994-03-04 1995-03-03 Process for making monoacetals of hydroquinone

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/US1995/002382 WO1995023778A2 (en) 1994-03-04 1995-02-27 Process for making monoacetals of hydroquinone

Country Status (8)

Country Link
EP (1) EP0748306A1 (en)
JP (1) JPH09509946A (en)
KR (1) KR970701684A (en)
CN (1) CN1145616A (en)
AU (2) AU1932295A (en)
CA (1) CA2184252C (en)
CZ (1) CZ257096A3 (en)
WO (2) WO1995023778A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
AU2006259056A1 (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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1423073A (en) * 1973-01-17 1976-01-28 Ciba Geigy Ag Amines and processes for their manufacture

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1423073A (en) * 1973-01-17 1976-01-28 Ciba Geigy Ag Amines and processes for their manufacture

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
H. G. KRISHNAMURTY ET AL: "Cleavage of aryl benzyl ethers by heterogeneous catalytic transfer hydrogenation", INDIAN JOURNAL OF CHEMISTRY, SECTION B, vol. 25B, 1986, NEW DELHI, pages 1253 - 1254 *
S. HANESSIAN ET AL: "Facile cleavage of benzyl ethers by catalytic transfer hydrogenation", SYNTHESIS., no. 5, May 1981 (1981-05-01), STUTTGART DE, pages 396 - 397 *
T. BIEG ET AL: "Cleavage of 2-phenyl-1,3-dioxolanes by catalytic transfer hydrogenation", SYNTHESIS., no. 4, April 1986 (1986-04-01), STUTTGART DE, pages 317 - 318 *
T. BIEG ET AL: "Removal of O-benzyl protective groups by catalytic transfer hydrogenation", SYNTHESIS., no. 1, January 1985 (1985-01-01), STUTTGART DE, pages 76 - 77 *

Also Published As

Publication number Publication date
WO1995023778A2 (en) 1995-09-08
EP0748306A1 (en) 1996-12-18
CA2184252A1 (en) 1995-09-08
JPH09509946A (en) 1997-10-07
WO1995023779A2 (en) 1995-09-08
AU1939595A (en) 1995-09-18
AU1932295A (en) 1995-09-18
WO1995023778A3 (en) 1995-09-28
KR970701684A (en) 1997-04-12
MX9603877A (en) 1997-09-30
CA2184252C (en) 1999-12-07
CN1145616A (en) 1997-03-19
CZ257096A3 (en) 1997-06-11

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