2-Hydroxybenzaldehyde (Salicylaldehyde) to 1,2-Benzenediol (Catechol)

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Query Query HO

1. Query

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Date

12 reactions in Reaxys

2018-03-25 08h:21m:00s (EST)

HO

HO O

Search as: As drawn, No salts, No mixtures

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HO

O

HO

HO

Rx-ID: 609334 View in Reaxys 1/12 Yield 98 %

Conditions & References With dihydrogen peroxide, Time= 0.666667h, T= 20 °C , Green chemistry, Dakin Phenol Oxidation, Time Saikia, Bishwajit; Borah, Parinita; Barua, Nabin Chandra; Green Chemistry; vol. 17; nb. 9; (2015); p. 4533 4536 View in Reaxys

98 %

With dihydrogen peroxide in water, Time= 2h, T= 20 °C , Green chemistry, Dakin Phenol Oxidation Saikia, Bishwajit; Borah, Parinita; RSC Advances; vol. 5; nb. 128; (2015); p. 105583 - 105586 View in Reaxys

92 %

With 7,8-difluoro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine, dihydrogen peroxide, sodium hydrogencarbonate in methanol, water, Time= 1h, T= 20 °C , Dakin oxidation Chen, Shuai; Hossain, Mohammad S.; Foss, Frank W.; Organic Letters; vol. 14; nb. 11; (2012); p. 2806 - 2809 View in Reaxys

91 %

With sodium percarbonate in tetrahydrofuran, water, Time= 5h, ultrasonication; other hydroxylated benzaldehydes and acetophenones Kabalka, G. W.; Reddy, N. K.; Narayana, C.; Tetrahedron Letters; vol. 33; nb. 7; (1992); p. 865 - 866 View in Reaxys

91 %

With sodium percarbonate in tetrahydrofuran, water, Time= 5h, ultrasonication Kabalka, G. W.; Reddy, N. K.; Narayana, C.; Tetrahedron Letters; vol. 33; nb. 7; (1992); p. 865 - 866 View in Reaxys

91 %

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, 1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine, oxygen, sodium hydrogencarbonate in water, acetonitrile, Time= 72h, T= 20 °C , Dakin Phenol Oxidation, Solvent Chen, Shuai; Foss, Frank W.; Organic Letters; vol. 14; nb. 19; (2012); p. 5150 - 5153,4 View in Reaxys

88%

4 : Preparation of catechol EXAMPLE 4 Preparation of catechol 6.1 g (0.05 mol) of salicylaldehyde and 33 g of a 12.6percent strength (0.13 mol) aqueous hydrogen peroxide solution are reacted for 70 hours at 50° C. and worked up analogously to Example 1, but without addition of base. 5.4 g of a solid are obtained, which is identified as catechol by 1 H-NMR spectroscopy with reference to a comparison sample. (Purity determined by gas chromatography: 90percent; yield 88percent of theory). With dihydrogen peroxide Patent; Hoechst Aktiengesellschaft; US5364983; (1994); (A1) English View in Reaxys

71 %

With dihydrogen peroxide, methyltrioxorhenium(VII) in ethanol, Time= 24h, Ambient temperature Yamazaki, Shigekazu; Chemistry Letters; nb. 2; (1995); p. 127 - 128 View in Reaxys

60 %

With alkaline hydrogen peroxide in water Kiong, Lam Soot; Tyman, John H. P.; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1981); p. 1942 - 1952 View in Reaxys

32 %

With menadione, sodium hydrogencarbonate, sodium L-ascorbate in ethanol, water, Time= 48h, T= 20 °C , p= 760.051Torr , pH= 8.5, Darkness, Green chemistry

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Silveira-Dorta, Gastón; Monzón, Diego M.; Crisóstomo, Fernando P.; Martín, Tomás; Martín, Víctor S.; Carrillo, Romen; Chemical Communications; vol. 51; nb. 32; (2015); p. 7027 - 7030 View in Reaxys With sodium hydroxide, dihydrogen peroxide in water, T= 37 °C , Rate constant Hocking, M. B.; Bhandari, K.; Shell, B.; Smyth, T. A.; Journal of Organic Chemistry; vol. 47; nb. 22; (1982); p. 4208 - 4215 View in Reaxys With peroxomonophosphoric acid in ethanol, water, T= 25 °C , var. reagents, Rate constant Ogata, Yoshiro; Sawaki, Yasuhiko; Tsukamoto, Yasuyuki; Bulletin of the Chemical Society of Japan; vol. 54; nb. 7; (1981); p. 2061 - 2064 View in Reaxys With dihydrogen peroxide, acetic acid v. Wacek; Eppinger; v. Bezard; Chemische Berichte; vol. 73; (1940); p. 521,528 View in Reaxys v.Wacek; Eppinger; Chemische Berichte; vol. 73; (1940); p. 644,651 View in Reaxys With sodium peroxide, water Dakin; American Chemical Journal; vol. 42; (1909); p. 495 View in Reaxys With barium peroxide, water Dakin; American Chemical Journal; vol. 42; (1909); p. 495 View in Reaxys Reaktion ueber mehrere Stufen Organic Syntheses; View in Reaxys 163 mg

With 9Na(1+)*4SO4 (2-)*Cl(1-)*2H2O2=4Na2SO4*2H2O2*NaCl in methanol, Time= 0.833333h, T= 70 °C Gayakwad, Eknath M.; Patil, Vilas V.; Shankarling, Ganapati S.; New Journal of Chemistry; vol. 41; nb. 7; (2017); p. 2695 - 2701 View in Reaxys

H C

13

H 13C H 13C

13

C H

13C

OH

HO

13C

HO

O

H

13C 13C

13C

13C

13CH 13CH

H

Rx-ID: 38014799 View in Reaxys 2/12 Yield 63 %

Conditions & References With dihydrogen peroxide, sodium hydroxide in water, T= 30 - 40 °C , Inert atmosphere, Dakin Phenol Oxidation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys

HO

HO

2-chloro-benzenediazonium-(1)-chloride

1.2-bis-<4-methyl-valeryloxy>-benzene HO

O

Rx-ID: 18019062 View in Reaxys 3/12 Yield

Conditions & References Reaction Steps: 2 1: SeO2, 30percent aq. H2O2 / 2-methyl-propan-2-ol / 4 h / Ambient temperature

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2: aq. K2CO3 / methanol / 1 h / Ambient temperature With selenium(IV) oxide, dihydrogen peroxide, potassium carbonate in methanol, tert-butyl alcohol Guzman; Mendoza; Garcia; Garibay; Oliveras; Maldonado; Synthetic Communications; vol. 25; nb. 14; (1995); p. 2121 - 2133 View in Reaxys

HO

HO

HO HO

OH

HO

O

O HO

Rx-ID: 2705112 View in Reaxys 4/12 Yield

Conditions & References

26 %, 28 %, 20 %

With lt;(Ce2(p-tert-butylcalix(8)arene))(Me2SO)5gt;*2Me2SO, dihydrogen peroxide in acetonitrile, Time= 5h, Ambient temperature Chawla, H. Mohindra; Hooda, Usha; Singh, Veena; Journal of the Chemical Society, Chemical Communications; nb. 5; (1994); p. 617 - 618 View in Reaxys

HO H

O

O

O

OH

HO

H HO

O

Rx-ID: 5820100 View in Reaxys 5/12 Yield

Conditions & References v. Wacek; Eppinger; v. Bezard; Chemische Berichte; vol. 73; (1940); p. 521,528 View in Reaxys v.Wacek; Eppinger; Chemische Berichte; vol. 73; (1940); p. 644,651 View in Reaxys

N

HO H

O

O

HO

HO

O H HO

O

HO

Rx-ID: 6076049 View in Reaxys 6/12 Yield

Conditions & References v. Wacek; Eppinger; v. Bezard; Chemische Berichte; vol. 73; (1940); p. 521,528 View in Reaxys v.Wacek; Eppinger; Chemische Berichte; vol. 73; (1940); p. 644,651 View in Reaxys

HO H

O

O

O

HO

HO

O

H

O

HO

HO

Rx-ID: 6076050 View in Reaxys 7/12 Yield

Conditions & References bei Siedetemperatur v. Wacek; Eppinger; v. Bezard; Chemische Berichte; vol. 73; (1940); p. 521,528 View in Reaxys v.Wacek; Eppinger; Chemische Berichte; vol. 73; (1940); p. 644,651 View in Reaxys T= 120 °C v. Wacek; Eppinger; v. Bezard; Chemische Berichte; vol. 73; (1940); p. 521,528 View in Reaxys v.Wacek; Eppinger; Chemische Berichte; vol. 73; (1940); p. 644,651

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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View in Reaxys

HO H

O

O

HO

HO

O

palladium-catalyst

H

HO

O

HO

Rx-ID: 6076051 View in Reaxys 8/12 Yield

Conditions & References T= 25 °C v. Wacek; Eppinger; v. Bezard; Chemische Berichte; vol. 73; (1940); p. 521,528 View in Reaxys v.Wacek; Eppinger; Chemische Berichte; vol. 73; (1940); p. 644,651 View in Reaxys

HO

O

HO

O O

HO

N O

O HO

O

O

Rx-ID: 608214 View in Reaxys 9/12 Yield

Conditions & References Dakin; American Chemical Journal; vol. 42; (1909); p. 495 View in Reaxys

HO H

O

O

HO

H

O

HO

Rx-ID: 5820099 View in Reaxys 10/12 Yield

Conditions & References in alkal.Loesung Dakin; American Chemical Journal; vol. 42; (1909); p. 495 View in Reaxys

HO H

O

H

HO

barium peroxide HO

O

Rx-ID: 5820107 View in Reaxys 11/12 Yield

Conditions & References Dakin; American Chemical Journal; vol. 42; (1909); p. 495 View in Reaxys

HO H

O

H

HO

sodium peroxide HO

O

Rx-ID: 5820126 View in Reaxys 12/12 Yield

Conditions & References Dakin; American Chemical Journal; vol. 42; (1909); p. 495 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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