Reaxys
PubChem
eMolecules
Reactions (11)
Yield
Substances (2)
Citations (22)
Conditions
References
1
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Rx-ID: 23144596 Find similar reactions
99.3%
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Stage #1: hydroquinone With 1,1'-bis-(diphenylphosphino)ferrocene in diethylene glycol dimethyl ether
T=100°C; AutoclaveInert atmosphere; Stage #2: oxirane in diethylene glycol dimethyl ether
T=130 - 135°C; 4 h; SolventTemperature; Hide Experimental Procedure
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Zhejiang Real Huangma Technology Co., Ltd.; Jin, yifeng; yan, jixiao; ma, dinglian; jin, hongcai
Patent: CN105523905 A, 2016 ; Location in patent: Paragraph 0023; 0057; 0058; 0059 ; Title/Abstract Full Text Show Details
9:Example 9
432 g of the diethylene glycol dimethyl ether obtained in Example 9 was recovered, together with 550 g of hydroquinone,1,1'-bis (diphenylphosphine) ferrocene 1.0g was charged into a reaction kettle and evacuated by means of a vacuum pump,The air inside the reaction kettle was replaced with nitrogen, and the temperature was raised under nitrogen protection after replacing three timesTo 100 , insulation 3-4 hours, the kettle completely material. When the hydroquinone is completely finished,The temperature was then evacuated for 20 minutes to remove the low boiling point substance in the kettle and then continued to the ringEthylene oxide 506g, added within 5 hours, the control reaction temperature of 130-135 ° C, the reactor pressureForce in -0.05-0.4Mpa, plus 4 hours after the end of incubation to continue the reaction; reaction is completed, cooling to80 ° C, vacuum degassing to remove unreacted ethylene oxide, the mother liquor gradually heated to 120 ° C by minusPressure distillation 7 hours in the product, the solvent vapor cooling can be re-applied after receiving.The product was detected by analysis: hydroquinone dihydroxyethyl ether content of 99.1percent, unreacted pairsThe color of the sample was 20 and the hydroxyl value was determined to be 559.8 mg KOH / g. 73%
With anion exchange resin A (Cl-type) in 2-methoxy-ethanol; toluene
T=100°C; 6 h; Hide Experimental Procedure
Hirano, Yoshiaki; Yamamoto, Hiroshi; Kubo, Takafumi; Nagano, Hideaki; Kitajima, Mitsuhiro; Yamaguchi, Hiroko
Patent: US2004/181099 A1, 2004 ; Location in patent: Page 15-16 ;
Title/Abstract Full Text Show Details
2-5:EXAMPLES 2-3, 2-4, and 2-5 [0164] Experiments were carried out in the same manner as in Example 2-1 by varying the reaction conditions. The reaction conditions and reaction results are shown in Table 1. Note that EQ was added for 3 hours in Examples 2-4 and 2-5. 69 %Chromat.
With anion exchange resin A (Cl-type) in 2-methoxy-ethanol
T=100°C; 4.5 h; Hide Experimental Procedure
Hirano, Yoshiaki; Yamamoto, Hiroshi; Kubo, Takafumi; Nagano, Hideaki; Kitajima, Mitsuhiro; Yamaguchi, Hiroko
Patent: US2004/181099 A1, 2004 ; Location in patent: Page 15-16 ; Title/Abstract Full Text Show Details
2-4:EXAMPLES 2-3, 2-4, and 2-5 [0164] Experiments were carried out in the same manner as in Example 2-1 by varying the reaction conditions. The reaction conditions and reaction results are shown in Table 1. Note that EQ was added for 3 hours in Examples 2-4 and 2-5.
2
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With lithium aluminium tetrahydride in tetrahydrofuran
RefluxInert atmosphere;
Rx-ID: 30469164 Find similar reactions
Ito, Yosuke; Tomiyasu, Yuichi; Kawanabe, Takahiro; Uemura, Keisuke; Ushimizu, Yuu; Nishino, Hiroshi
Organic and Biomolecular Chemistry, 2011 , vol. 9, # 5 p. 1491 - 1507 Title/Abstract Full Text View citing articles Show Details
3
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Multi-step reaction with 2 steps 1: potassium carbonate / acetone / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / Reflux; Inert atmosphere View Scheme
Rx-ID: 30469252 Find similar reactions
Ito, Yosuke; Tomiyasu, Yuichi; Kawanabe, Takahiro; Uemura, Keisuke; Ushimizu, Yuu; Nishino, Hiroshi
Organic and Biomolecular Chemistry, 2011 , vol. 9, # 5 p. 1491 - 1507 Title/Abstract Full Text View citing articles Show Details
4
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Rx-ID: 718417 Find similar reactions
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74%
Stage #1: hydroquinone With sodium hydroxide in water
2 h; Inert atmosphereReflux; Stage #2: 2-chloro-ethanol in water
40 h; RefluxInert atmosphere;
Yang, Wanggui; Xia, Ping Fang; Wong, Man Shing
Organic Letters, 2010 , vol. 12, # 18 p. 4018 - 4021 Title/Abstract Full Text View citing articles Show Details
60%
With sodium hydroxide in water
24 h; Heating;
Ikeda, Taichi; Asakawa, Masumi; Miyake, Koji; Shimizu, Toshimi
Chemistry Letters, 2004 , vol. 33, # 11 p. 1418 - 1419 Title/Abstract Full Text View citing articles Show Details
With sodium hydroxide
T=130°C;
Imp. Chem. Ind.
Patent: US2044083 , 1934 ; Full Text Show Details
With sodium hydroxide; calcium carbonate
Imp. Chem. Ind.
Patent: US2044083 , 1934 ; Full Text Show Details
With sodium hydroxide
Inert atmosphere;
Li, Ya-Fei; Tang, Kuan-Zhen; Tang, Yu; Liu, Wei-Sheng; Tan, Min-Yu
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2008 , vol. 71, # 3 p. 1153 - 1157 Title/Abstract Full Text View citing articles Show Details
5
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Rx-ID: 27870738 Find similar reactions
98%
With urea; sodium carbonate; zinc oxide
T=180°C; 3 h; Product distribution / selectivity; Hide Experimental Procedure
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Dai, Shenghong A.; Lin, Hsing-Yo; Wen, Chien-Sheng
Patent: US2008/228010 A1, 2008 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details
9:
EXAMPLE 9; To a three-neck 250 mL round bottom flask, equipped with a magnetic stirrer, thermometer, and reflux condenser, was charged with hydroquinone (11.0 g, 0.1 mol), ethylene glycol (21.1 g, 0.34 mol), sodium carbonate (0.2 g, 1.88 mmol), urea (15.0 g, 0.25 mol) and ZnO (0.2 g, 2.46 mmol). Then the reaction mixture was heated to 180° C. for 3 hours, and then cooled to room temperature. The reaction mixture was extracted with ethyl acetate. Organic solvent was removed from the filtered organic phase by a vacuum evaporator to afford crude product (19.4 g, 98percent yield). 1H NMR (R=H. a=1. b=1), d=2.04 (s. 2H. -OH), 3.79 (t. 4H), 3.95 (t. 4H), 6.84 (s. 4H. aromatics). 85%
With sodium carbonate; urea; zinc oxide
T=170 - 190°C;
Lin, Hsing-Yo; Dai, Shenghong A.
Journal of the Chinese Chemical Society, 2010 , vol. 57, # 2 p. 167 - 173 Title/Abstract Full Text View citing articles Show Details
6
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With sodium tetrahydroborate in ethanol
T=0 - 20°C;
Rx-ID: 29951233 Find similar reactions
Twibanire, Jean-D'Amour K.; Al-Mughaid, Hussein; Grindley, T. Bruce
Tetrahedron, 2010 , vol. 66, # 50 p. 9602 - 9609 Title/Abstract Full Text View citing articles Show Details
7
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With hydrogenchloride in methanol; dichloromethane
4 h; Ambient temperature;
Rx-ID: 5122983 Find similar reactions
Gibson, Harry W.; Nagvekar, Devdatt S.; Delaviz, Yadollah; Bryant, William S.
Canadian Journal of Chemistry, 1998 , vol. 76, # 10 p. 1429 - 1436 Title/Abstract Full Text View citing articles Show Details
8
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Rx-ID: 16442159 Find similar reactions
Gibson, Harry W.; Nagvekar, Devdatt S.; Delaviz, Yadollah; Bryant, William S.
1: NaOH, sodium dithionite / butan-1-ol / 30 h / Heating 2: conc. HCl / methanol; CH2Cl2 / 4 h / Ambient temperature View Scheme
9
Canadian Journal of Chemistry, 1998 , vol. 76, # 10 p. 1429 - 1436 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 33687 Find similar reactions
89%
With sodium hydride in N,N-dimethyl-formamide
T=140°C;
Pirrung, Michael C.; Nunn, David S.
Tetrahedron, 1996 , vol. 52, # 16 p. 5707 - 5738 Title/Abstract Full Text View citing articles Show Details
With 1,4-dioxane; N-benzyl-trimethylammonium hydroxide
Dyer; Scott
Journal of the American Chemical Society, 1957 , vol. 79, p. 672,674 Full Text Show Details
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With sodium hydride in N,N-dimethyl-formamide
Pirrung, Michael C.; Nunn, David S.
Tetrahedron Letters, 1988 , vol. 29, # 2 p. 163 - 166 Title/Abstract Full Text View citing articles Show Details
10
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Rx-ID: 5861498 Find similar reactions
Kalvoda,L.
Collection of Czechoslovak Chemical Communications, 1973 , vol. 38, p. 1679 - 1692 Full Text View citing articles Show Details
Koppers Company, USA
Patent: DE1958725 , 1970 ; Chem.Abstr., vol. 73, # 55802 Full Text Show Details
Sakakibara et al.
Kogyo Kagaku Zasshi, 1970 , vol. 73, p. 1196,1197, 1200 Chem.Abstr., 1970 , vol. 73, # 88523 Full Text Show Details
Mitsui Petrochemical Industries, Ltd.
Patent: JP6927570 , 1967 ; Chem.Abstr., 1970 , vol. 72, # 90052g Full Text Show Details
BASF
Patent: DE1096366 , 1958 ; Chem.Abstr., 1961 , # 21056 Full Text Show Details
Hoechst AG
Patent: DE1920032 , 1970 ; Full Text Show Details
A
B
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11
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With ethanol
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Shukis; Tallman
Journal of the American Chemical Society, 1944 , vol. 66, p. 1462 Full Text View citing articles Show Details
Read; Miller
Journal of the American Chemical Society, 1932 , vol. 54, p. 1195 Full Text View citing articles Show Details