2-'ALK'benzene-1,4-diol by Asch

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PubChem

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Reactions (322)

Yield

Substances (32)

Citations (235)

Conditions

References

100

Synthesize Find similar Multi-step reaction with 4 steps 2: diethyl ether / anschliessendes Behandeln mit Aethylenoxid 3: KOH 4: platinum; methanol / Hydrogenation.Erwaermen des Reaktionsprodukts mit einem KationenAustauscher in Methanol View Scheme

101

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Rx-ID: 22353347 Find similar reactions

Stern et al.

Journal of the American Chemical Society, 1957 , vol. 79, p. 5797,5800 Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

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Rx-ID: 22407341 Find similar reactions

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

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102

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Rx-ID: 23665744 Find similar reactions

Stage #1: With polyethylene glycol; carbon; copper(II) nitrate; anhydrous magnesium carbonate

T=390 480°C; P=760.051 Torr; 24.25 h; Calcination; Stage #2: methanol; hydroquinone With water in ethylene glycol dimethyl ether

T=465 - 480°C; 10 - 24 h; Gas phase; Product distribution / selectivity; Hide Experimental Procedure

GENERAL ELECTRIC COMPANY

Patent: WO2005/97721 A1, 2005 ; Location in patent: Page/Page column 9-10 ; Title/Abstract Full Text Show Details

1; 2-10:

A dry mixture of 100 grams (gms) of magnesium carbonate, 2.5 gms of polyethylene glycol, 1 gram (gm) graphite, and 1000 ppm of copper nitrate was prepared. This mixture was pelletized and crushed to particles having a size of 800 - 1400 micrometers to provide the catalyst precursor system. Examples 2- 10: A glass reactor was loaded with 5 grams of the catalyst precursor system prepared in example 1. The catalyst was calcined in-situ for 22 hours at 390°C under a flow of nitrogen, at atmospheric pressure. After calcination, the temperature was increased to 480°C over a period of two hours under a nitrogen atmosphere. After 15 minutes, a feed mixture comprising hydroquinone, methanol (MeOH), monoglyme and water, was introduced at the flow rates indicated by the weighted hourly space velocity (WHSV) in Table 1. The molar ratio of hydroquinone to monoglyme to water was maintained at 1:2:3 and the carrier gas to hydroquinone molar ratio was maintained at 8:1. The temperature of the feed mixture and the molar ratio of methanol to hydroquinone were varied as indicated in Table 1. The alkylation was run for 24 hours under the above mentioned conditions during which methyl hydroquinone selectivity and dimethyl hydroquinone selectivity were monitored on HPLC. Samples for measuring conversion and selectivity were withdrawn as indicated by the time of sampling (TOS) data indicated in Table 1 below. 2-Methyl hydroquinone selectivity was calculated as follows: 2-MeHQ selectivity=(moles of 2MeHQ formed/moles of HQ converted) *100 percent. Table 1 Ex. HQ in moles MeOH/HQ Time of sampling WHSV Temp HQ 2-MeHQ 2,6-di Me HQ in hours in °C conversion selectivity in selectivity in in mole percent molepercent mole percent 1 1 3 10 1.3 480 25 75 13 2 1 2 10 1 480 50 32 20 3 1 3 10 1.3 465 27 53 15 4 1 4 10 1.6 480 30 55 26 5 1 2 10 1.6 480 24 63 10 61 1 3 10 1.3 480 38 44 17 72 1 3 24 1.3 480 15 64 13 Hydrogen as the carrier gas 25 moles of water per mole of hydroquinone. Stage #1: With carbon; anhydrous magnesium carbonate

Calcination; Stage #2: methanol; hydroquinone With water in ethylene glycol dimethyl ether

T=480°C; 10 h; Gas phase; Product distribution / selectivity; Hide Experimental Procedure

GENERAL ELECTRIC COMPANY

Patent: WO2005/97721 A1, 2005 ; Location in patent: Page/Page column 10-11 ; Title/Abstract Full Text Show Details

Comparative Example. A similar procedure was followed as in examples 2-10, except that the catalyst precursor contained only magnesium carbonate. Results are shown in Table 2. Table 2. Ex. HQ in MeOH/HQ Time of WHSV Temp HQ 2-MeHQ 2,6-di Me HQ moles sampling in °C conversi selectivity in selectivity in in hours on in molepercent mole percent mole percent Comp 10 15 Ex. 1 1 3 1.3 480 34 49 15

103

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Inert atmosphere;

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Rx-ID: 28897044 Find similar reactions

Gholap, Shivajirao L.; Woo, Christina M.; Ravikumar; Herzon, Seth B.

Organic Letters, 2009 , vol. 11, # 19 p. 4322 - 4325 Title/Abstract Full Text View citing articles Show Details

104

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With triethylsilane; trifluoroacetic acid in dichloromethane

T=0 - 20°C; 15 h; Hide Experimental Procedure

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Rx-ID: 34875917 Find similar reactions

JUBILANT BIOSYS LTD.; SARMA, Pakala Kumara Savithru; ACHARYA, Vinod Parameshwaran; KASIBHATLA, Srinivas Rao; VISWANADHAN, Vellarkad Narayana; TIWARI, Atul; SINGHA, Rakesh Kumar; BISCHOFF, Alexander

Patent: WO2012/90219 A2, 2012 ; Location in patent: Page/Page column 83 ; Title/Abstract Full Text Show Details

Intermediate I. XXXIII

2-Ethyl-benzene-l ,4-diol2-Ethyl-benzene-l ,4-diolTrifluoroaceticacid ( 120 ml, 1623 mmol) was added dropwise to a solution of 2-( I - Hydroxy-ethyl)-benzene- l ,4-diol (intermediate LXXXII) (25 g, 162 mmol), triethylsi lane (26 ml, 162 mmol) in 250 ml of dichloromethane at 0 °C. The reaction mixture was stirred at room temperature for 1 5 hour. Then the reaction mixture was quenched with ice-cold water and evaporated the solvent. The residue was taken in water and extarcted with ethyl acetate. The comboned organic extract was washed with water, brine, dried over anhydrous sodium sulphate and evaporated. The crude material was purified using column chromatography (si lica gel 100-200 mesh, 10:90 ethylacetate:hexane) to afford 2-Ethylbenzene- l , 4-diol in 89 percent yield.

105

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With Re2O7 in dichloromethane

T=20°C; Dienone-Phenol Rearrangement;

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Rx-ID: 40168130 Find similar reactions

Xia, Zilei; Hu, Jiadong; Shen, Zhigao; Yao, Qizheng; Xie, Weiqing

RSC Advances, 2015 , vol. 5, # 48 p. 38499 - 38502 Title/Abstract Full Text View citing articles Show Details

106

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10%

With Candida antarctica lipase B in di-isopropyl ether; isopropyl alcohol

T=45°C; 1 h; Enzymatic reaction; regioselective reaction;

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Rx-ID: 41790038 Find similar reactions

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei

Canadian Journal of Chemistry, 2015 , vol. 94, # 1 p. 44 - 49 Title/Abstract Full Text View citing articles Show Details

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107

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Rx-ID: 6731844 Find similar reactions

Einwirkung von Sonnenlicht;

Angeletti

Atti della Accademia delle Scienze di Torino, Classe di Scienze Fisiche, Matematiche e Naturali, 1934 , vol. # 70, p. 326,328 Full Text Show Details

108

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bei der Reduktion;

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Rx-ID: 287527 Find similar reactions

Bayrac

Bulletin de la Societe Chimique de France, 1895 , vol. <3> 13, p. 979 Annales de Chimie (Cachan, France), 1897 , vol. <7> 10, p. 66,73 Full Text Show Details

Bayrac

Bulletin de la Societe Chimique de France, 1895 , vol. <3> 13, p. 979

Annales de Chimie (Cachan, France), 1897 , vol. <7> 10, p. 66,73 Full Text Show Details

109

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With sulfuric acid; aluminium

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Rx-ID: 306346 Find similar reactions

Eastman Kodak Co.

Patent: US2533203 , 1948 ; Full Text Show Details

110

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Rx-ID: 551318 Find similar reactions

With carbon disulfide; aluminium trichloride

Kochen des Reaktionsprodukts mit wss. HCl und amalgamiertem Zink;

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Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

111

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Rx-ID: 718212 Find similar reactions

With Fuller's Earth

T=175 - 195°C;

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Bush Inc.

Patent: US2291804 , 1939 ; Full Text Show Details

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112

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With hydrogen; copper (II) chromite in ethanol

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Rx-ID: 4122546 Find similar reactions

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

113

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Rx-ID: 4321971 Find similar reactions

With sulfuric acid

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Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

114

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Rx-ID: 4685773 Find similar reactions

64%

With lithium chloride in various solvent(s) T=160 - 170°C; 1 h;

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Ozaki, Yutaka; Hosoya, Ayako; Okamura, Kyouko; Kim, Sang-Won

Synlett, 1997 , vol. 1997, # 4 p. 365 - 366 Title/Abstract Full Text View citing articles Show Details

115

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Rx-ID: 5809724 Find similar reactions

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Calcott; Tinker; Weinmayr

Journal of the American Chemical Society, 1939 , vol. 61, p. 1010,1014 Full Text Show Details

116

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Rx-ID: 5809725 Find similar reactions

T=175 - 195°C;

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Bush Inc.

Patent: US2291804 , 1939 ; Full Text Show Details

117

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T=70 - 80°C;

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Rx-ID: 6675340 Find similar reactions

Baddeley; Kenner

Journal of the Chemical Society, 1934 , p. 633 Full Text Show Details

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118

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Rx-ID: 7180014 Find similar reactions

2-Allyl-hydrochinon, H2 (Pd-C) in E.;

Kaufman et al.

Journal of Organic Chemistry, 1967 , vol. 32, p. 504 Full Text View citing articles Show Details

2-Propionyl-hydrochinon, H2 (Pd-C);

Armstrong et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 1928,1932 Full Text Show Details

119

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Rx-ID: 7180015 Find similar reactions

With hydrogenchloride; amalgamated zinc

Johnson; Hodge

Journal of the American Chemical Society, 1913 , vol. 35, p. 1019 Full Text Show Details

120

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Rx-ID: 7180016 Find similar reactions

With water; iron(III) chloride

Schuetteln des Reaktionsprodukts mit wss. H2SO3;

Baddeley; Kenner

Journal of the Chemical Society, 1934 , p. 633 Full Text Show Details

121

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Rx-ID: 7180017 Find similar reactions

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Johnson; Hodge

Journal of the American Chemical Society, 1913 , vol. 35, p. 1019 Full Text Show Details

122

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T=70 - 80°C;

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Rx-ID: 7180018 Find similar reactions

Baddeley; Kenner

Journal of the Chemical Society, 1934 , p. 633 Full Text Show Details

123

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Rx-ID: 7247850 Find similar reactions

entspr. Phenol, Persulfat;

Balba; Casida

Journal of Agricultural and Food Chemistry, 1968 , vol. 16, p. 561,562,563 Full Text View citing articles Show Details

Bei Rk. v. Cumene mit H2O2/HF/CO2;

Vesely; Schmerling

Journal of Organic Chemistry, 1970 , vol. 35, p. 4028,4030 Full Text Show Details

6-Hydroxy-4-methylcoumarin (1h), NaOH, Ethandiol;

Dhekne et al.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1977 , vol. 15, p. 755 Full Text Show Details

Hide Details

Hydrochinon, Isopropylalkohol, ZnCl2 in wss. HCl (6 h, 86-98grad);

Bogoljubskii

J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 869,862 Chem.Abstr., 1963 , vol. 58, # 2391 Full Text Show Details

2-Isopropyl-phenol in NaOH u. K-Persulfat (0grad=;

Bogoljubskii

J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 869,862 Chem.Abstr., 1963 , vol. 58, # 2391 Full Text Show Details

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124

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Rx-ID: 7437650 Find similar reactions

Eastman Kodak Co.

Patent: US2533203 , 1948 ;

Full Text Show Details

125

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A: 15% B: 15 % Chromat.

in tetrahydrofuran

Heating;

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Shahidzadeh, Mansour; Ghandi, Mehdi

Journal of Organometallic Chemistry, 2001 , vol. 625, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

126

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35%

T=180°C; P=20 Torr;

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Rx-ID: 10461780 Find similar reactions

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

127

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Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

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Rx-ID: 22407342 Find similar reactions

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

128

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With hydrogen; palladium in methanol

Hide Experimental Procedure

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Rx-ID: 24365202 Find similar reactions

Merck and Co., Inc.

Patent: US6090836 A1, 2000 ; Title/Abstract Full Text Show Details

25.C:Step C

Step C Preparation of 2-propylhydroquinone: 6.8 grams (28.4 mmole, 1.0 eq.) of product from step B was dissolved in 60 ml of methanol. 680 mg of 10percent palladium on carbon (0.64 mmole, 0.023 eq.) was added and the stirring suspension was evacuated and charged with hydrogen. After 16 hours the catalyst was filtered over celite and the filtrate evaporated.

The title compound (4.3 grams) was recovered by recrystallization from dichloromethane/hexanes. NMR (400 MHz, CD3 OD) δ 6.56 (d, 1H), 6.51 (d, 1H), 6.43 (dd, 1H), 2.48 (t, 2H), 1.58 (m, 2H), 0.96 (t, 3H).

129

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With Candida antarctica lipase B in di-isopropyl ether; isopropyl alcohol

T=45°C; 1 h; Enzymatic reaction; regioselective reaction;

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Rx-ID: 41790042 Find similar reactions

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei

Canadian Journal of Chemistry, 2015 , vol. 94, # 1 p. 44 - 49 Title/Abstract Full Text View citing articles Show Details

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130

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A: 31 % Spectr. B: 69 % Spectr.

With hydrogenchloride; sodium cyanoborohydride in tetrahydrofuran

18 h; Product distribution;

Elliger, Carl A.

Synthetic Communications, 1985 , vol. 15, # 14 p. 1315 - 1324 Title/Abstract Full Text Show Details

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131

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Rx-ID: 2703605 Find similar reactions

ether, THF, -78 deg C; 60 min; Yield given. Multistep reaction. Yields of byproduct given;

Fischer, A.; Henderson, N.

Tetrahedron Letters, 1980 , vol. 21, p. 701 - 704

Title/Abstract Full Text View citing articles Show Details

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132

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A: 9% B: 91%

With methyllithium in tetrahydrofuran; diethyl ether

T=-78°C; 1 h;

Fischer, A.; Henderson, N.

Tetrahedron Letters, 1980 , vol. 21, p. 701 - 704 Title/Abstract Full Text View citing articles Show Details

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133

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Rx-ID: 6221169 Find similar reactions

Bamberger; Blangey

Justus Liebigs Annalen der Chemie, 1911 , vol. 384, p. 291 Chemische Berichte, 1903 , vol. 36, p. 1627 Full Text Show Details

134

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With sulfuric acid; aluminium

T=95°C;

Synthesize Find similar Eastman Kodak Co.

Patent: US2533203 , 1948 ;

Rx-ID: 270314 Find similar reactions

Full Text Show Details

135

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With sodium hydroxide; dipotassium peroxodisulfate

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Rx-ID: 340829 Find similar reactions

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

136

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Rx-ID: 718403 Find similar reactions

137

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With phosphoric acid; xylene

T=105°C;

Eastman Kodak Co.

Patent: US2722556 , 1952 ;

With aluminum oxide; silica gel; xylene

T=200°C;

Universal Oil Prod. Co.

Patent: US2781404 , 1953 ;

With aluminium tris-lt;4-hydroxyphenolategt;; xylene

T=240°C;

Stroh et al.

Angewandte Chemie, 1957 , vol. 69, p. 699,700 Full Text Show Details

Full Text Show Details

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Rx-ID: 718427 Find similar reactions

With zinc(II) chloride

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Eastman Kodak Co.

Patent: US2511193 , 1947 ; Full Text Show Details

With phosphoric acid; xylene

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Eastman Kodak Co.

Patent: US2722556 , 1952 ; Full Text Show Details

With phosphoric acid in water

T=69 - 83°C; 3 h; Hide Experimental Procedure

Zhao, Jianying

Patent: CN105541560 A, 2016 ; Location in patent: Paragraph 0011 ; Title/Abstract Full Text Show Details

The synthesis process of the crude TBHQ of the present embodiment comprises the following steps:

1) 5 parts by weight of phosphoric acid and 0.5 part by weight of water were poured into a stirring tank, and then 4 parts by weight of hydroquinone was added to the stirring cylinder,(2) After stirring, the mixed solution is put into a reaction kettle and heated to 69 DEG C, and 10 parts by weight of t-butanol are added to the reaction kettle;In this case,(3) heating to 83 ° C while maintaining heating for 3 hours to carry out the reaction;(4) the reaction product by centrifugal separation, washing, dehydration obtained after TBHQ crude.TBHQ crude synthetic process, can be directly prepared TBHQ crude, without further processing, process is simple, accurate measurement data, easy to implement.

138

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With N-(N-L-γ-glutamyl-L-cysteinyl)glycine

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Rx-ID: 1985073 Find similar reactions

Mizuno, Masashi; Toda, Masaya; Danno, Gen-ichi; Kanazawa, Kazuki; Natake, Masato

Agricultural and Biological Chemistry, 1988 , vol. 52, # 11 p. 2843 - 2850 Title/Abstract Full Text Show Details

139

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3 h; Ambient temperature; Yield given;

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Rx-ID: 3211653 Find similar reactions

Gayo, Leah M.; Winters, Michael P.; Moore, Harold W.

Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6896 - 6899 Title/Abstract Full Text View citing articles Show Details

140

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Rx-ID: 3388492 Find similar reactions

With silica gel in dichloromethane

T=30°C; 24 h; Product distribution;

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Kamitori, Yasuhiro; Hojo, Masaru; Masuda, Ryoichi; Izumi, Tatsuo; Tsukamoto, Shuichi

Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4161 - 4165 Title/Abstract Full Text View citing articles Show Details

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141

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in water

T=22°C; Irradiation; Equilibrium constantRate constant;

Dohrmann, Juergen K.; Bergmann, Barbara

Journal of Physical Chemistry, 1995 , vol. 99, # 4 p. 1218 - 1227 Title/Abstract Full Text View citing articles Show Details

142

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With hydrogen; copper (II) chromite in ethanol

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Rx-ID: 4122639 Find similar reactions

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

143

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Rx-ID: 4331473 Find similar reactions

in diethyl ether

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Florjanczyk,Z. et al.

Journal of Organometallic Chemistry, 1976 , vol. 112, p. 21 - 28 Full Text View citing articles Show Details

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144

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in water

T=22°C; Rate constant;

Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf; Michel, Christa; Saran, Manfred

Journal of the Chemical Society - Faraday Transactions, 1998 , vol. 94, # 13 p. 1835 - 1840 Title/Abstract Full Text View citing articles Show Details

145

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Rx-ID: 5959834 Find similar reactions

Fujita; Sano

Journal of Organic Chemistry, 1979 , vol. 44, p. 2647,2648, 2650 Full Text View citing articles Show Details

Ruetgerswerke AG

Patent: DE1159961 , 1962 ; Chem.Abstr., 1964 , vol. 60, # 7955f Full Text Show Details

Bayer AG

Patent: US3051762 , 1958 ;

Chem.Abstr., 1963 , vol. 58, # 1402f Full Text Show Details

Hide Experimental Procedure

Kurita Water Industries Ltd.

Patent: US5079000 A1, 1992 ; Title/Abstract Full Text Show Details

A method as claimed in claim 3, in which the host compound is at least one compound selected from the group consisting of the following substances: ... 4,4'-Butylidene-bis(3-methyl-6-t-butylphenol) 2,2'-Methylene-bis(4-methyl-6-t-butylphenol) 4. 4'-Thio-bis(3-methyl-6-t-butylphenol) 2,2'-Methylenbis(4-chlorophenol) T-butylhydroquinone 2,5-Di-t-butylhydroquinone.

Hide Experimental Procedure

Adams Veterinary Research Laboratories

Patent: US4668666 A1, 1987 ; Title/Abstract Full Text Show Details

butylated hydroxytoluene (BHT) tert-butylhydroquinone (TBHQ) Ethoxyquin ascorbic acid ascorbic palmitate Hide Details

Hide Experimental Procedure

Givaudan Corporation

Patent: US4713473 A1, 1987 ; Title/Abstract Full Text Show Details

(a) an alkylphenol selected from the group consisting essentially of: ... 2-isopropenyl-5-methylphenol, 4-tert.octylphenol, nonylphenol, dodecylphenol di-tert.butyl-hydroxy-toluene (BHT), tert.butyl-hydroxy-anisole (BHA), and tert.butyl-hydroquinone (TBHQ); or,

Hide Experimental Procedure

Ciba Geigy Corporation

Patent: US4519805 A1, 1985 ; Title/Abstract Full Text Show Details

Type (A) compounds are for example the following: ... hydroquinone-monobenzyl ether, 5-methyl-resorcin, 4-cyclohexyl-resorcin, 2,5-di-(tert-amyl)-hydroquinone, tert-butyl-hydroquinone,

Hide Experimental Procedure

NIPPON SODA CO., LTD.

Patent: EP1113112 A1, 2001 ; Title/Abstract Full Text Show Details

(20) A slime preventing/removing agent according to (19), in which the multi-molecular host compound is one or more compounds selected from the group consisting of the following compounds: tetrakisphenols ... 2,2'-methylenebis(4-chlorophenol), deoxycholic acid, cholic acid,

α, α, α', α'-tetraphenyl-1,1'-biphenyl-2,2'-dimethanol, t-butylhydroquinone, 2,5-di-tert-butylhydroquinone,

146

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Rx-ID: 7178249 Find similar reactions

Hydrochinon, Butylalkohol, ZnCl2, 5h, 185-190grad;

Bogoljubskii

Journal of Organic Chemistry USSR (English Translation), 1966 , vol. 2, p. 1420 Zhurnal Organicheskoi Khimii, 1966 , vol. 2, p. 1433 Full Text Show Details

2-<2,5-Dimethoxy-phenyl>-butan, HBr;

Bogoljubskii

Journal of Organic Chemistry USSR (English Translation), 1966 , vol. 2, p. 1420 Zhurnal Organicheskoi Khimii, 1966 , vol. 2, p. 1433 Full Text Show Details

1,4-Benzochinon, Tri-<butyl-(2)>-boran, sd. Ae., N2, ca. 1 h;

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

Hide Details

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

(yield)94percent;

147

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Rx-ID: 7250432 Find similar reactions

Benzochinon-(1,4), Tributylboran, sd. Ae., N2, ca. 1 h;

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

(yield)86percent;

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

148

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Rx-ID: 7250433 Find similar reactions

With hydrogenchloride; amalgamated zinc

Gulland

Biochemical Journal, 1932 , vol. 26, p. 32,43 Full Text Show Details

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

149

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Rx-ID: 7250434 Find similar reactions

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

150

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Rx-ID: 7279863 Find similar reactions

Hydrochinon, Toluol, Al-isopropylat, Isobutylen;

Ethyl Corp.

Patent: US3075832 , 1958 ; Chem.Abstr., 1963 , vol. 59, # 12706 Full Text Show Details

1,4-Benzochinon, Tri-(2-methyl-propyl)-boran, sd.

Hawthorne; Reintjes

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Ae., N2, ca. 1 h;

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

(yield)91percent;

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

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151

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With ruthenium trichloride in water; acetonitrile

Oxidation; Hydrolysis; Electrochemical reaction;

Michman, Michael; Oron, Miriam; Schaefer, Hans J.

Collection of Czechoslovak Chemical Communications, 2000 , vol. 65, # 6 p. 924 - 940 Title/Abstract Full Text View citing articles Show Details

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152

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Rx-ID: 8900892 Find similar reactions

A: 15% B: 26 % Chromat.

in tetrahydrofuran

Heating;

Shahidzadeh, Mansour; Ghandi, Mehdi

Journal of Organometallic Chemistry, 2001 , vol. 625, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

153

Synthesize

Rx-ID: 10462596

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37%

T=180°C; P=20 Torr;

Find similar

Find similar reactions

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

154

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Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

Synthesize Find similar

Rx-ID: 22407347 Find similar reactions

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

155

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Rx-ID: 23058877 Find similar reactions

With formic acid

T=25°C; 336 - 3696 h; Conversion of starting material; Hide Experimental Procedure

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Aasbo, Kari; Granli, Tom; Breivik, Harald

Patent: US2004/10166 A1, 2004 ; Location in patent: Page 4 ; Title/Abstract Full Text Show Details

2:EXAMPLE 2; Preparation of TBHQ

BHA was dissolved in 85percent methanoic acid to give a concentration of 0.75percent by weight BHA and the solution was then stored at room temperature (25° C.). Analysis by HPLC and 1H-NMR spectroscopy at regular time intervals gave the following results:- [TABLE-US-00001] Elapsed time percent by weight BHA 2 weeks 0.72 5 weeks 0.69 10 weeks 0.15 22 weeks 0.10 [0041] Conversion of BHA to TBHQ was confirmed by 1H-NMR spectroscopy.

With formic acid

24 h; Heating / reflux; Hide Experimental Procedure

Aasbo, Kari; Granli, Tom; Breivik, Harald

Patent: US2004/10166 A1, 2004 ; Location in patent: Page 3-4 ; Title/Abstract Full Text Show Details

1:EXAMPLE 1; Preparation of TBHQ

BHA (1.5 g) was dissolved in 85percent methanoic acid (100 ml) and the solution was heated with continuous stirring. After refluxing for about 24 hours, analysis by 1H-NMR spectroscopy revealed that ether cleavage had taken place to produce a solution of TBHQ in 85percent methanoic acid. A

156

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A: 97% B: 0.7%

With dihydrogen peroxide; Ti-superoxide in water; acetic acid

T=50 - 60°C; 1.25 h; Product distribution / selectivity; Hide Experimental Procedure

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COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH

Patent: WO2005/63664 A1, 2005 ; Location in patent: Page/Page column 7 ; Title/Abstract Full Text Show Details

Preparation of 2-tert-butyl-1, 4-benzoquinone A mixture of 2-t-butylphenol (5 mmol) and Ti-superoxide catalyst (125 mg, 20percent w/w) in acetic acid (5 ml) was heated with stirring at 50-60 C under inert atmosphere. To this reaction mixture was added aq. 30percent H202 (20 mmol) drop wise over 15 min. and heated for 1 h. The catalyst was recovered by simple filtration and 2tert-butyl-1, 4-benzoquinone formed (97percent) was separated by chromatographic purification.Table 1: Ti-superoxide (1) catalyzed oxidation of phenols to quinines and hydroquinones with aq. 30percent H202 : a Ex. Substrate t/h Conversion ProductU Selectivity (percent) c No. (percent)

Quinone HQd 1. Phenol 10 22 2 20e 91. 0 2. Phenol 8 66 5 6 92. 4 3. Phenol 7 65 3 60 92.3 4. Phenol 7 68 3.5 63g 92.7 5. Phenol 1 92 88 2.3 95.7 6. o-Cresol 1 99 96 3.0 97.0 7. 7n-Cresol 1 100 99 0.5 99.0 8. 2,6-Dimethylphenol 1 100 97 2.0 97.0 9. 2-'Butylphenol 1 99 97 0. 7 98.0 10. 2, 6-Dibutylphenol 3 70 65 2. 0 93.0 11.4-Chlorophenol 1 57 55-96.5 12.4-Bromophenol 1 61 60-98. 4 13. 4-Iodophenol 1 77 75-97.4 14.2, 4-Dichlorophenol 1 32 25 5. 0 78.1 (a) See examples for detailed experimental procedure; (b) determined by GC analysis of the crude product; (c) selectivity to hydroquinone ; (d) hydroquinone; (e) aq. 10percent H202; (f) aq.50percent H202; (g) 40percent w/w catalyst.

157

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85%

With platinum (II) chloride in methanol; ethylene glycol dimethyl ether

T=50°C;

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Rx-ID: 29050252 Find similar reactions

Kim, Ikyon; Kim, Kyungsun; Choi, Jungeun

Journal of Organic Chemistry, 2009 , vol. 74, # 21 p. 8492 - 8495 Title/Abstract Full Text View citing articles Show Details

158

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Rx-ID: 29110946

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77%

With anhydrous iron chloride; potassium phosphate; tetrabutylammomium bromide; Nmethyl-2-(methylamino)ethylamine in water

T=180°C; P=5250.53 Torr; 20 h;

Find similar

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Ren, Yunlai; Cheng, Lin; Tian, Xinzhe; Zhao, Shuang; Wang, Jianji; Hou, Chaodong

Tetrahedron Letters, 2010 , vol. 51, # 1 p. 43 - 45 Title/Abstract Full Text View citing articles Show Details

159

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With hydrogen; palladium on activated charcoal

Hide Experimental Procedure

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Rx-ID: 33258202 Find similar reactions

STRATEGIC ENZYME APPLICATIONS, INC.; ALBIZATI, Kim; TRACEWELL, Cara

Patent: WO2012/75053 A2, 2012 ; Location in patent: Page/Page column 79 ; Title/Abstract Full Text Show Details

Example 6 - Generation of t-Butylhydroquinone [00338] Lignin is converted into t-butylhydroquinone by first contacting lignin with molecular oxygen and laccase, followed by H2/H20 to generate 1,2,4-trihydroxybenzene. Next, the 1,2,4-trihydroxybenzene is optionally isolated from the lignin. Then, the 1,2,4- trihydroxybenzene is treated with isobutylene and acid (e.g., HCl). Finally, the alkylated intermediate is subjected to hydro geno lysis conditions (i.e., hydrogen and Pd/C catalyst) to generate t-butylhydroquinone.

160

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161

Multi-step reaction with 2 steps 1: Acidic conditions 2: hydrogen / palladium on activated charcoal View Scheme

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Rx-ID: 33258207 Find similar reactions

STRATEGIC ENZYME APPLICATIONS, INC.; ALBIZATI, Kim; TRACEWELL, Cara

Patent: WO2012/75053 A2, 2012 ; Title/Abstract Full Text Show Details

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Rx-ID: 34649549 Find similar reactions

With 3-(4-sulfobutylamino)propylsilanized MCM41 in nitrobenzene

T=150°C; Friedel-Crafts Alkylation; 0.166667 h; Microwave irradiationGreen chemistry; Catalytic behavior; TemperatureSolventTime; chemoselective reaction; Hide Experimental Procedure

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Ng, Eng-Poh; Mohd Subari, Siti Norbayu; Marie, Olivier; Mukti, Rino R.; Juan, Joon-Ching

Applied Catalysis A: General, 2013 , vol. 450, p. 34 - 41 Title/Abstract Full Text View citing articles Show Details

2.5. Catalytic experiments

Friedel–Crafts reactions were performed with microwave irradiation assistance by modifying the synthesis condition [30]. Prior to reaction, hydroquinone (Merck, 2.0 mmol), methyl tert-butyl ether (MTBE, Merck, 2.0 mmol) and freshly activated SO3H-MCM-41 catalyst (0.1 g, 100 °C, 3 h) were loaded into a reactor. The reaction was realized in an Anton Paar Synthos 3000 microwave oven under magnetic stirring and 300 W microwave irradiation, while the reaction temperature was monitored by an infrared pyrometer. The samples were withdrawn after the reaction and the liquid phase was separated and analyzed using a gas chromatograph (Hewlett-Packard 5880) equipped with a Carbowax Equity 1 non-polar capillary column. The identity of the product was confirmed by GC–MS (Perkin-Elmer GC-IR 2000 system).

162

Synthesize Find similar With Candida antarctica lipase B in di-isopropyl ether; isopropyl alcohol

T=45°C; Enzymatic reaction; regioselective reaction;

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Rx-ID: 41790043 Find similar reactions

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei

Canadian Journal of Chemistry, 2015 , vol. 94, # 1 p. 44 - 49 Title/Abstract Full Text View citing articles Show Details

163

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Rx-ID: 43243684 Find similar reactions

99.9%

With sulfuric acid

T=85°C; 8 h; Large scale; Temperature; Hide Experimental Procedure

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Thanksgiving Food Science and Tecnology Co., Ltd. of Dongguan City; Wang, Li

Patent: CN105294403 A, 2016 ; Location in patent: Paragraph 0027; 0028 ; Title/Abstract Full Text Show Details

Reaction1 Hydroquinone 110kg 116kg acetic acid tert-ester and sulfuric acid concentration of 50percent sulfuric acid 294kg added to the reaction kettle was warmed up to 85 ° C to a reaction for 8 hours to complete the reaction, cooling to 65 °C rear centrifugal filtration, filtrate recycling sulfuric acid, the resulting added 1 times warm water washing, the crude product of tert-butyl hydroquinone, wherein the tert-butyl hydroquinone content is 70percent. A

164

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Rx-ID: 5810450 Find similar reactions

T=75°C; Oxydation;

Fichter; Simon

Helvetica Chimica Acta, 1934 , vol. 17, p. 717,719 Full Text Show Details

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165

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With n-butyllithium; N,N,N',N,tetramethylethylenediamine

1.) THF, 5-15 deg C, sonication, 2 h, 2.) r.t., several hours; Yield given. Multistep reaction. Yields of byproduct given;

Saa, Jose M.; Morey, Jeroni; Suner, Guillem; Frontera, Antoni; Costa, Antoni

Tetrahedron Letters, 1991 , vol. 32, # 49 p. 7313 - 7316 Title/Abstract Full Text View citing articles Show Details

166

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Rx-ID: 8282606 Find similar reactions

Bamberger

Justus Liebigs Annalen der Chemie, 1920 , vol. 420, p. 137 Full Text Show Details

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167

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Rx-ID: 7066325 Find similar reactions

Fierz-David; Blangey; Streiff

Helvetica Chimica Acta, 1946 , vol. 29, p. 1718,1758 Full Text Show Details

168

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Rx-ID: 7066326 Find similar reactions

Fierz-David; Blangey; Streiff

Helvetica Chimica Acta, 1946 , vol. 29, p. 1718,1758 Full Text Show Details

169

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A: 0.1 g

With diazomethane in diethyl ether

5 deg C, 3 h, then r.t. overnight; Yields of

Conway, Gregory A.; Loeffler, Larry J.

Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 1315 - 1320

byproduct given;

Title/Abstract Full Text Show Details

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170

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With water

T=20°C; Irradiation;

Chaikovskaya; Sokolova; Karetnikova; Mal'Kov; Kuz'Mina

Russian Journal of Applied Chemistry, 2009 , vol. 82, # 3 p. 396 - 401 Title/Abstract Full Text View citing articles Show Details

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171

Synthesize Find similar Rx-ID: 11244695 Find similar reactions

A: 81.6% B: 4.5% C: 13.9%

With isopropyl alcohol; Candida antarctica lipase B; immobilized in di-isopropyl ether

T=45°C; 1 h; Title compound not separated from byproducts.;

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

172

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With hydrogenchloride; amalgamated zinc

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Rx-ID: 468909 Find similar reactions

Quilico et al.

Gazzetta Chimica Italiana, 1950 , vol. 80, p. 325,331, 342 Full Text Show Details

173

Synthesize Find similar With hydrogen; copper (II) chromite in ethanol

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Rx-ID: 4122659 Find similar reactions

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

174

Synthesize Find similar With potassium hydroxide; hydrazine hydrate; 1,2bis-(2-hydroxyethoxy)-ethane

Heating;

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Rx-ID: 4304314 Find similar reactions

Lisa,E. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3307 - 3312 Full Text View citing articles Show Details

175

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Rx-ID: 4319090 Find similar reactions

With phosphoric acid in xylene

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Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

176

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100%

With boron tribromide in dichloromethane

T=-78 - 20°C; 4 h; Inert atmosphere; Hide Experimental Procedure

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Rx-ID: 4344068 Find similar reactions

The University of Chicago; MRKSICH, Milan; HODNELAND, Christian

Patent: US2015/369816 A1, 2015 ; Location in patent: Paragraph 0201 ; Title/Abstract Full Text Show Details

12:n-Pentylhydroquinone 21.

To the solution of 2.4 g (11.5 mmol) of n-Pentyldimethoxybenzene 1 in CH2Cl2 at −78° C., 5.4 ml (5 eq) of BBr3 was added dropwise. After warming to room temperature, the reaction mixture was stirred for 4 hr. The BBr3 was quenched with ethyl ether at −78° C., and then with water at room temperature. Extraction with CH2Cl2 and silicagel chromatography (hexane:EA=2:1) gave 2.07 g (quant.) of 21 as a white solid.

80%

With aluminium trichloride in benzene

8 h; Heating;

Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

177

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With hydrogenchloride; amalgamated zinc

Rx-ID: 7183875 Find similar reactions

Stoughton; Baltzly; Bass

Journal of the American Chemical Society, 1934 , vol. 56, p. 2007 Full Text View citing articles Show Details

Asahina; Yasue

Chemische Berichte, 1936 , vol. 69, p. 643,647 Yakugaku Zasshi, 1936 , vol. 56, p. 549,554 Full Text Show Details

Stoughton; Baltzly; Bass

Journal of the American Chemical Society, 1934 , vol. 56, p. 2007 Full Text View citing articles Show Details

Asahina; Yasue

Chemische Berichte, 1936 , vol. 69, p. 643,647 Yakugaku Zasshi, 1936 , vol. 56, p. 549,554 Full Text Show Details

178

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Rx-ID: 7446310 Find similar reactions

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Stoughton; Baltzly; Bass

Journal of the American Chemical Society, 1934 , vol. 56, p. 2007 Full Text View citing articles Show Details

Asahina; Yasue

Chemische Berichte, 1936 , vol. 69, p. 643,647 Yakugaku Zasshi, 1936 , vol. 56, p. 549,554 Full Text Show Details

179

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Rx-ID: 7559664 Find similar reactions

Tucker; Pack

Journal of Agricultural and Food Chemistry, 1972 , vol. 20, p. 412,413 Full Text Show Details

(1-Chlor-1-methylbutyl)-dibenzyl-hydrochinon, Hydrierung;

180

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Rx-ID: 7646927 Find similar reactions

2,5-Dihydroxy-isovalerophenon, Eg., konz. HCl, ZnAmalgam, Siedetemp., 12 Std.;

Chari et al.

Indian Journal of Chemistry, 1969 , vol. 7, p. 40,41 Full Text Show Details

2-(3,3-Dimethyl-allyl)-hydrochinon, wfr. E., H2, Pt;

Chari et al.

Indian Journal of Chemistry, 1969 , vol. 7, p. 40,41

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Full Text Show Details

181

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With hydrogenchloride; amalgamated zinc

Rx-ID: 7646928 Find similar reactions

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

182

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Hydrochinon, tert.-Amylalkohol, 85percentig. H3PO4;

Rx-ID: 7647169 Find similar reactions

Perrotti; Castelfranchi

Chimica e l'Industria (Milan, Italy), 1960 , vol. 42, p. 1333,1338 Full Text Show Details

183

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Rx-ID: 7982288 Find similar reactions

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Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

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184

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Rx-ID: 7982289 Find similar reactions

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Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

185

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Rx-ID: 7982290 Find similar reactions

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Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

186

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Rx-ID: 7982291 Find similar reactions

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Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

187

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Rx-ID: 7982292 Find similar reactions

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Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

188

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Multi-step reaction with 3 steps 2: Raney Ni 3: 80 percent / AlCl3 / benzene / 8 h / Heating View Scheme

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Rx-ID: 17925202 Find similar reactions

Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

189

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Multi-step reaction with 4 steps 1: AlCl3

3: Raney Ni 4: 80 percent / AlCl3 / benzene / 8 h / Heating View Scheme

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Rx-ID: 17933634 Find similar reactions

Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

190

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Multi-step reaction with 2 steps 1: Raney Ni 2: 80 percent / AlCl3 / benzene / 8 h / Heating View Scheme

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Rx-ID: 17947957 Find similar reactions

Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

191

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Multi-step reaction with 4 steps 1: AlCl3

3: Raney Ni 4: 80 percent / AlCl3 / benzene / 8 h / Heating View Scheme

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Rx-ID: 17960924 Find similar reactions

Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

192

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Multi-step reaction with 4 steps 1: AlCl3; CS2; benzene / Behandeln des Reaktionsprodukts mit wss.HCl und Essigsaeure 2: palladium; ethanol / Hydrogenation 3: Raney nickel; methanol / Hydrogenation 4: amalgamated zinc; aqueous HCl View Scheme

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Rx-ID: 22237771 Find similar reactions

Quilico et al.

Gazzetta Chimica Italiana, 1950 , vol. 80, p. 325,331, 342 Full Text Show Details

193

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Multi-step reaction with 2 steps 1: Raney nickel; methanol / Hydrogenation 2: amalgamated zinc; aqueous HCl View Scheme

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Rx-ID: 22256050 Find similar reactions

Quilico et al.

Gazzetta Chimica Italiana, 1950 , vol. 80, p. 325,331, 342 Full Text Show Details

194

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Multi-step reaction with 3 steps 1: palladium; ethanol / Hydrogenation 2: Raney nickel; methanol / Hydrogenation 3: amalgamated zinc; aqueous HCl View Scheme

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Rx-ID: 22262031 Find similar reactions

Quilico et al.

Gazzetta Chimica Italiana, 1950 , vol. 80, p. 325,331, 342 Full Text Show Details

195

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Rx-ID: 22275740 Find similar reactions

Quilico et al.

Gazzetta Chimica Italiana, 1950 , vol. 80, p. 325,331, 342 Full Text Show Details

196

Synthesize Find similar Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

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Rx-ID: 22407343 Find similar reactions

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

197

Synthesize Find similar Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

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Rx-ID: 22416327 Find similar reactions

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

198

Synthesize Find similar Multi-step reaction with 2 steps 1: aq. HBr / acetic acid 2: aq. N2H4, KOH, triethylene glycol / Heating View Scheme

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Rx-ID: 22777427 Find similar reactions

Lisa,E. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3307 - 3312 Full Text View citing articles Show Details