DE69516083T2 - Verfahren zur Herstellung von acylsubstituierten Resorcinolen - Google Patents
Verfahren zur Herstellung von acylsubstituierten ResorcinolenInfo
- Publication number
- DE69516083T2 DE69516083T2 DE69516083T DE69516083T DE69516083T2 DE 69516083 T2 DE69516083 T2 DE 69516083T2 DE 69516083 T DE69516083 T DE 69516083T DE 69516083 T DE69516083 T DE 69516083T DE 69516083 T2 DE69516083 T2 DE 69516083T2
- Authority
- DE
- Germany
- Prior art keywords
- acyl
- substituted resorcinols
- preparation
- resorcinols
- substituted
- 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 - Lifetime
Links
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 11
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 40
- -1 transition metal Lewis acid Chemical class 0.000 claims description 18
- 239000002841 Lewis acid Substances 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 229910052723 transition metal Inorganic materials 0.000 claims description 14
- GOZHNJTXLALKRL-UHFFFAOYSA-N (5-benzoyl-2,4-dihydroxyphenyl)-phenylmethanone Chemical class OC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 GOZHNJTXLALKRL-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 11
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 10
- 230000003197 catalytic effect Effects 0.000 claims description 8
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 235000005074 zinc chloride Nutrition 0.000 claims description 6
- 239000011592 zinc chloride Substances 0.000 claims description 6
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical group ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- SUQGLJRNDJRARS-UHFFFAOYSA-N (3-benzoyloxyphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C=1)=CC=CC=1OC(=O)C1=CC=CC=C1 SUQGLJRNDJRARS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- KLAKIAVEMQMVBT-UHFFFAOYSA-N p-hydroxy-phenacyl alcohol Natural products OCC(=O)C1=CC=C(O)C=C1 KLAKIAVEMQMVBT-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/336,135 US5567850A (en) | 1994-11-08 | 1994-11-08 | Method for making acyl substituted resorcinols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69516083D1 DE69516083D1 (de) | 2000-05-11 |
| DE69516083T2 true DE69516083T2 (de) | 2000-09-14 |
Family
ID=23314728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69516083T Expired - Lifetime DE69516083T2 (de) | 1994-11-08 | 1995-10-24 | Verfahren zur Herstellung von acylsubstituierten Resorcinolen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5567850A (enExample) |
| EP (1) | EP0711744B1 (enExample) |
| JP (1) | JP3884784B2 (enExample) |
| CN (1) | CN1067371C (enExample) |
| DE (1) | DE69516083T2 (enExample) |
| ES (1) | ES2144580T3 (enExample) |
| SG (1) | SG63524A1 (enExample) |
| TW (1) | TW317563B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5981073A (en) * | 1997-01-16 | 1999-11-09 | General Electric Company | Compounds based on dibenzoylresorcinol, and related compositions and articles |
| KR100453590B1 (ko) * | 2001-10-17 | 2004-10-20 | 주식회사 바이오랜드 | 벤젠 디올의 모노카르보닐화 방법 |
| CN100439307C (zh) * | 2003-07-08 | 2008-12-03 | 荷兰联合利华有限公司 | 化妆活性物质的制备方法 |
| CN103159608A (zh) * | 2011-12-14 | 2013-06-19 | 南京华狮化工有限公司 | 一种间苯二酚烷基酮的制备方法 |
| CN107879910B (zh) * | 2017-11-02 | 2021-06-11 | 武汉科技大学 | 一种2,4-二羟基二苯甲酮的绿色合成工艺 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2794052A (en) * | 1957-05-28 | Process for the preparation of diacyl | ||
| US1750299A (en) * | 1925-04-16 | 1930-03-11 | Sharp & Dohme Inc | Production of acyl resorcinols |
| US2891996A (en) * | 1956-04-23 | 1959-06-23 | Dow Chemical Co | 2, 4-dihydroxy benzophenone derivatives |
| US3769349A (en) * | 1967-01-27 | 1973-10-30 | Kyodo Chem Co Ltd | Process for preparing 2,4-dihydroxybenzophenones |
| US3526666A (en) * | 1968-01-12 | 1970-09-01 | Ferro Corp | Synthesis of 2-hydroxy-4-alkoxybenzophenones |
| DE2616479C2 (de) * | 1976-04-14 | 1986-12-04 | Brickl, Rolf, Dr., 7951 Warthausen | Substituierte Fluoracylresorcine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel und Kosmetika |
| DE2963903D1 (en) * | 1978-12-05 | 1982-11-25 | Fisons Plc | A process for the production of 2-alkyl- or 2-alkenyl-4,6-diacetyl resorcinols; 2-allyl-4,6-diacetyl resorcinol |
| JPS61180738A (ja) * | 1985-02-06 | 1986-08-13 | Nippon Zeon Co Ltd | アルキル（ジヒドロキシフエニル）ケトンの製造法 |
| DE3904371A1 (de) * | 1989-02-14 | 1990-08-16 | Basf Ag | Verfahren zur herstellung von 2,4-dihydroxybenzophenon |
-
1994
- 1994-11-08 US US08/336,135 patent/US5567850A/en not_active Expired - Lifetime
-
1995
- 1995-06-08 TW TW084105836A patent/TW317563B/zh not_active IP Right Cessation
- 1995-08-03 SG SG1995001040A patent/SG63524A1/en unknown
- 1995-10-24 EP EP95307549A patent/EP0711744B1/en not_active Expired - Lifetime
- 1995-10-24 ES ES95307549T patent/ES2144580T3/es not_active Expired - Lifetime
- 1995-10-24 DE DE69516083T patent/DE69516083T2/de not_active Expired - Lifetime
- 1995-11-06 JP JP28630895A patent/JP3884784B2/ja not_active Expired - Lifetime
- 1995-11-06 CN CN95118784.8A patent/CN1067371C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2144580T3 (es) | 2000-06-16 |
| EP0711744B1 (en) | 2000-04-05 |
| CN1131656A (zh) | 1996-09-25 |
| SG63524A1 (en) | 1999-03-30 |
| JPH08245488A (ja) | 1996-09-24 |
| TW317563B (enExample) | 1997-10-11 |
| JP3884784B2 (ja) | 2007-02-21 |
| US5567850A (en) | 1996-10-22 |
| CN1067371C (zh) | 2001-06-20 |
| DE69516083D1 (de) | 2000-05-11 |
| EP0711744A1 (en) | 1996-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |