e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

The Journal of Organic Chemistry

Preparation and reactions of dianions from cresols

RB Bates, TJ Siahaan

Index: Bates, Robert B.; Siahaan, Teruna J. Journal of Organic Chemistry, 1986 , vol. 51, # 9 p. 1432 - 1434

Full Text: HTML

Citation Number: 35

Abstract

With n-BuLilKO-t-Bu, protons are removed from the hydroxyl and methyl groups of cresols 5 to give dianions 6 in yields of 85%(ortho), 95%(meta), and 42%(para). These dianions react with alkyl halides, Me3SiC1, Bu3SnC1, COz, and oxidizing agents at carbon only and with dialkyl sulfates at both carbon and oxygen. Thus phenol derivatives bearing primary alkyl groups can be prepared from the corresponding methylphenols via dianions

m-Cresol Structure

~%

3-[2-(3-hydroxyphenyl)ethyl]phenol Structure

3-[2-(3-hydroxy...

3-(2,2-Dimethylpropyl)phenol Structure

3-(2,2-Dimethyl...

Propane,2-iodo-2-methyl- Structure

Propane,2-iodo-...

m-Cresol Structure

~%

3-[2-(3-hydroxyphenyl)ethyl]phenol Structure

3-[2-(3-hydroxy...

3-(2,2-Dimethylpropyl)phenol Structure

3-(2,2-Dimethyl...

2-Bromo-2-methylpropane Structure

2-Bromo-2-methy...

m-Cresol Structure

~%

3-[2-(3-hydroxyphenyl)ethyl]phenol Structure

3-[2-(3-hydroxy...

3-(2,2-Dimethylpropyl)phenol Structure

3-(2,2-Dimethyl...

m-Cresol Structure

2-(brommethyl)naphthalen Structure

2-(brommethyl)n...

~%

3-[2-(3-hydroxyphenyl)ethyl]phenol Structure

3-[2-(3-hydroxy...

2-(3-hydroxy-β-phenethyl)naphthalene Structure

2-(3-hydroxy-β-...

m-Cresol Structure

2-Bromopropane Structure

~%

3-[2-(3-hydroxyphenyl)ethyl]phenol Structure

3-[2-(3-hydroxy...

3-ISO-BUTYLPHENOL Structure

3-ISO-BUTYLPHENOL

p-Cresol Structure

~%

4-(2,2-DIMETHYLPROPYL)-PHENOL Structure

4-(2,2-DIMETHYL...

Phenol,4,4'-(1,2-ethanediyl)bis- Structure

Phenol,4,4'-(1,...

p-Cresol Structure

Propane,2-iodo-2-methyl- Structure

Propane,2-iodo-...

~%

4-(2,2-DIMETHYLPROPYL)-PHENOL Structure

4-(2,2-DIMETHYL...

Phenol,4,4'-(1,2-ethanediyl)bis- Structure

Phenol,4,4'-(1,...

p-Cresol Structure

2-Bromopropane Structure

~%

4-Isobutylphenol Structure

4-Isobutylphenol

Phenol,4,4'-(1,2-ethanediyl)bis- Structure

Phenol,4,4'-(1,...

3-Chloro-2-methyl-1-propene Structure

3-Chloro-2-meth...

~%

5-Chloro-4-(chloromethyl)-2,4-dimethyl-1-pentene Structure

5-Chloro-4-(chl...

4-(3-methylbut-3-enyl)phenol Structure

4-(3-methylbut-...

Phenol,4,4'-(1,2-ethanediyl)bis- Structure

Phenol,4,4'-(1,...

p-Cresol Structure

3-Chloro-2-methyl-1-propene Structure

3-Chloro-2-meth...

~%

5-Chloro-4-(chloromethyl)-2,4-dimethyl-1-pentene Structure

5-Chloro-4-(chl...

4-(3-methylbut-3-enyl)phenol Structure

4-(3-methylbut-...

Detail

1-Bromobutane Structure

p-Cresol Structure

~%

4-Pentylphenol Structure

N/A Structure

Detail

1-Bromobutane Structure

p-Cresol Structure

~%

4-Pentylphenol Structure

2-butyl-p-cresol Structure

2-butyl-p-cresol

Detail

o-cresol Structure

3-Chloro-2-methyl-1-propene Structure

3-Chloro-2-meth...

~%

5-Chloro-4-(chloromethyl)-2,4-dimethyl-1-pentene Structure

5-Chloro-4-(chl...

2-(3-methylbut-3-enyl)phenol Structure

2-(3-methylbut-...

3-Chloro-2-methyl-1-propene Structure

3-Chloro-2-meth...

~%

5-Chloro-4-(chloromethyl)-2,4-dimethyl-1-pentene Structure

5-Chloro-4-(chl...

4-(3-methylbut-3-enyl)phenol Structure

4-(3-methylbut-...

Phenol,4,4'-(1,2-ethanediyl)bis- Structure

Phenol,4,4'-(1,...

p-Cresol Structure

3-Chloro-2-methyl-1-propene Structure

3-Chloro-2-meth...

~%

5-Chloro-4-(chloromethyl)-2,4-dimethyl-1-pentene Structure

5-Chloro-4-(chl...

4-(3-methylbut-3-enyl)phenol Structure

4-(3-methylbut-...

Detail

m-Cresol Structure

3-Chloro-2-methyl-1-propene Structure

3-Chloro-2-meth...

~%

3-(3-METHYL-BUT-3-ENYL)-PHENOL Structure

3-(3-METHYL-BUT...

p-Cresol Structure

~%

4-(2,2-DIMETHYLPROPYL)-PHENOL Structure

4-(2,2-DIMETHYL...

Phenol,4,4'-(1,2-ethanediyl)bis- Structure

Phenol,4,4'-(1,...

p-Cresol Structure

Propane,2-iodo-2-methyl- Structure

Propane,2-iodo-...

~%

4-(2,2-DIMETHYLPROPYL)-PHENOL Structure

4-(2,2-DIMETHYL...

Phenol,4,4'-(1,2-ethanediyl)bis- Structure

Phenol,4,4'-(1,...

p-Cresol Structure

2-Bromopropane Structure

~%

4-Isobutylphenol Structure

4-Isobutylphenol

Phenol,4,4'-(1,2-ethanediyl)bis- Structure

Phenol,4,4'-(1,...

m-Cresol Structure

2-Bromopropane Structure

~%

3-[2-(3-hydroxyphenyl)ethyl]phenol Structure

3-[2-(3-hydroxy...

3-ISO-BUTYLPHENOL Structure

3-ISO-BUTYLPHENOL

m-Cresol Structure

Diethyl sulfate Structure

Diethyl sulfate

~%

Benzene, 1-ethoxy-3-methyl- Structure

Benzene, 1-etho...

N/A Structure

Chlorotrimethylsilane Structure

Chlorotrimethyl...

p-Cresol Structure

~%

4-TRIMETHYLSILANYLMETHYL-PHENOL Structure

4-TRIMETHYLSILA...

Biosynthesis and metabolism of plant hormones

[Cornforth; Robinson Journal of the Chemical Society, 1942 , p. 684,687]

Biosynthesis and metabolism of plant hormones

[Cornforth; Robinson Journal of the Chemical Society, 1942 , p. 684,687]

Biosynthesis and metabolism of plant hormones

[Cornforth; Robinson Journal of the Chemical Society, 1942 , p. 684,687]

Biosynthesis and metabolism of plant hormones

[Cornforth; Robinson Journal of the Chemical Society, 1942 , p. 684,687]