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All 4 posts Subject: H2O2 o-cresol to 2,5-dihydroxytoluene, 98% Please login to post Down

psyloxy
(Hive Addict)
05-06-04 19:03
No 505367
      H2O2 o-cresol to 2,5-dihydroxytoluene, 98%
(Rated as: excellent)

JOC 65,8.2000 - 2348 - Lot's a thanks to ning who retrieved the article!

Reaction of Phenol with H2O2 catalyzed by Cis-Cu.

cis-Bisglycinato copper(II) monohydrate (50mg, 0.225 mmol), phenol (473mg, 5.32 mmol), and H2O2 (1ml, 30%)
were mixed together in a flask and stirred at room temperature. The white paste obtained slowly turned brown, and
the color intensified with time. After 24h of continuous stirring, the reaction mixture was washed
several times with petroleum ether (4 x 20ml) to obtain a paste, and this paste was washed with water (1ml) and dried
in evacuated desiccator to obtain a black solid (0,24g).

Reaction of o-Cresol. Similar reaction of o-cresol
(540 mg, 5 mmol) with H2O2 (1ml 30%) and cis-Bisglycinato copper(II) monohydrate (50 mg, 0,225 mmol) gave
2,5-dihydroxytoluene in 98% yield

o-cresol from phenol, HCOH and Ca(OH)₂: Patent US2401608

preparation of cis-Bisglycinato copper(II) monohydrate
1. Weigh, to the nearest 0.01 g, 4g of copper (II) acetate monohydrate and place in a 250 ml flask. Add 40 ml of H2O and heat, with stirring, until the salt completely dissolves.
2. Keeping the solution warm, add 40 ml of hot 95% ethanol to the flask.
3. Weigh out 3 g of glycine and place in a 50 ml beaker. Add 40 ml H2O and heat until dissolution occurs.
4. Add the hot glycine solution to the hot copper solution and swirl.
5. Cool the flask in an ice bath until the product precipitates.
6. Collect the product using a Büchner funnel. The filtrate may be used to rinse out any product remaining in the flask.
7. Wash the product once with approximately 60 ml of 95% ethanol.
8. Suction dry the product for a few minutes, then put on a watch glass and dry in an oven at about 50ºC for 40 minutes.
9. Weigh the final, dry product and place in a pre-weighed vial (with cap).

Ref: http://wwwchem.uwimona.edu.jm%3A1104/lab_manuals/c31lex1.html

--psyloxy--

psyloxy
(Hive Addict)
05-11-04 20:31
No 506492
User Picture       o-cresol from potassium o-toluenesulphonate

Zeitschrift fuer Chemie 1869; p618

50g potassium o-toluenesulphonate and 150g KOH are molten in an iron pot/shuck, the molten mixture dissolved in water, treated with HCl, the dopped out o-cresol extracted with ether, the extract dried over CaCl₂, the ether stripped off and the left over o-cresol distilled in a carbonic acid stream. (<^__ What's that ? Steam distillation w/ added CO₂ ?)

yield: 62% (16g o-cresol from 50g o-TsOK)
--psyloxy--

moo
(Hive Bee)
05-11-04 21:21
No 506502
      I assume it means that it is distilled in a...

I assume it means that it is distilled in a CO₂ atmosphere to prevent oxidation.

_{fear fear hate hate}

ning
(acetaminophanatic)
05-12-04 05:29
No 506600
User Picture       Oh, there's going to bee some DOM a'cookin!

psyloxy, that's awesome!

Actually, almost anything can bust a phenol to a benzoquinone...MnO2, KMnO4, HNO3, I believe bleach can do it, and possible H2O2 with MnO2, Iron salts, or Copper salts. That funky ligand may not bee necessary.

This is really much better than the nitration way, because you don't have to distill nitrotoluenes! Cool.

_{...it's an AOL chatroom for dyslexic spider monkies...}

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	All 4 posts		Subject: H2O2 o-cresol to 2,5-dihydroxytoluene, 98%		Please login to post		Down


		psyloxy (Hive Addict) 05-06-04 19:03 No 505367				H2O2 o-cresol to 2,5-dihydroxytoluene, 98% (Rated as: excellent)
						JOC 65,8.2000 - 2348 - Lot's a thanks to ning who retrieved the article! Reaction of Phenol with H2O2 catalyzed by Cis-Cu. cis-Bisglycinato copper(II) monohydrate (50mg, 0.225 mmol), phenol (473mg, 5.32 mmol), and H2O2 (1ml, 30%) were mixed together in a flask and stirred at room temperature. The white paste obtained slowly turned brown, and the color intensified with time. After 24h of continuous stirring, the reaction mixture was washed several times with petroleum ether (4 x 20ml) to obtain a paste, and this paste was washed with water (1ml) and dried in evacuated desiccator to obtain a black solid (0,24g). Reaction of o-Cresol. Similar reaction of o-cresol (540 mg, 5 mmol) with H2O2 (1ml 30%) and cis-Bisglycinato copper(II) monohydrate (50 mg, 0,225 mmol) gave 2,5-dihydroxytoluene in 98% yield o-cresol from phenol, HCOH and Ca(OH)₂: Patent US2401608 preparation of cis-Bisglycinato copper(II) monohydrate 1. Weigh, to the nearest 0.01 g, 4g of copper (II) acetate monohydrate and place in a 250 ml flask. Add 40 ml of H2O and heat, with stirring, until the salt completely dissolves. 2. Keeping the solution warm, add 40 ml of hot 95% ethanol to the flask. 3. Weigh out 3 g of glycine and place in a 50 ml beaker. Add 40 ml H2O and heat until dissolution occurs. 4. Add the hot glycine solution to the hot copper solution and swirl. 5. Cool the flask in an ice bath until the product precipitates. 6. Collect the product using a Büchner funnel. The filtrate may be used to rinse out any product remaining in the flask. 7. Wash the product once with approximately 60 ml of 95% ethanol. 8. Suction dry the product for a few minutes, then put on a watch glass and dry in an oven at about 50ºC for 40 minutes. 9. Weigh the final, dry product and place in a pre-weighed vial (with cap). Ref: http://wwwchem.uwimona.edu.jm%3A1104/lab_manuals/c31lex1.html --psyloxy--



		psyloxy (Hive Addict) 05-11-04 20:31 No 506492				o-cresol from potassium o-toluenesulphonate
						Zeitschrift fuer Chemie 1869; p618 50g potassium o-toluenesulphonate and 150g KOH are molten in an iron pot/shuck, the molten mixture dissolved in water, treated with HCl, the dopped out o-cresol extracted with ether, the extract dried over CaCl₂, the ether stripped off and the left over o-cresol distilled in a carbonic acid stream. (<^__ What's that ? Steam distillation w/ added CO₂ ?) yield: 62% (16g o-cresol from 50g o-TsOK) --psyloxy--



		moo (Hive Bee) 05-11-04 21:21 No 506502				I assume it means that it is distilled in a...
						I assume it means that it is distilled in a CO₂ atmosphere to prevent oxidation. _{fear fear hate hate}



		ning (acetaminophanatic) 05-12-04 05:29 No 506600				Oh, there's going to bee some DOM a'cookin!
						psyloxy, that's awesome! Actually, almost anything can bust a phenol to a benzoquinone...MnO2, KMnO4, HNO3, I believe bleach can do it, and possible H2O2 with MnO2, Iron salts, or Copper salts. That funky ligand may not bee necessary. This is really much better than the nitration way, because you don't have to distill nitrotoluenes! Cool. _{...it's an AOL chatroom for dyslexic spider monkies...}

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