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methanol
2-methyl-2-phenylpropionic acid
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With sulfuric acid at 20 - 70℃; for 21.5h; Inert atmosphere; | 99.5% |
With sulfuric acid at 70℃; for 12h; | 94% |
With sulfuric acid Heating; |
benzeneacetic acid methyl ester
methyl iodide
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 24h; | 95% |
Stage #1: benzeneacetic acid methyl ester; methyl iodide With sodium hydride In tetrahydrofuran at 0 - 25℃; for 18h; Stage #2: With acetic acid In tetrahydrofuran at 0℃; | 85% |
Stage #1: benzeneacetic acid methyl ester; methyl iodide With sodium hydride In tetrahydrofuran at 0 - 25℃; for 18h; Stage #2: With acetic acid In tetrahydrofuran | 85% |
Conditions | Yield |
---|---|
Stage #1: Methyl isobutyrate With sodium hexamethyldisilazane In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: chlorobenzene With di-μ-bromobis(tri-tert-butylphosphino)dipalladium(I) In toluene at 100℃; for 4h; Inert atmosphere; | 92% |
d(4)-methanol
2-(2-bromophenyl)-2-methylpropionaldehyde
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With 2BF4(1+)*C27H50P2*2H(1+); palladium diacetate; caesium carbonate In toluene at 60℃; for 14h; Inert atmosphere; | 92% |
bromobenzene
1-methoxy-2-methyl-1-trimethylsiloxy-1-propene
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With zinc(II) fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 80℃; for 12h; | 91% |
With zinc(II) fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 80℃; for 12h; Product distribution; Further Variations:; Solvents; Reagents; | 93 % Chromat. |
methanol
2-(2-bromophenyl)-2-methylpropionaldehyde
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With 2BF4(1+)*C27H50P2*2H(1+); palladium diacetate; caesium carbonate In toluene at 60℃; for 14h; Inert atmosphere; | 91% |
2-methyl-2-phenylpropionic acid
carbonic acid dimethyl ester
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry; | 91% |
methanol
2-bromo-2-methyl-1-phenyl-propan-1-one
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With silver hexafluoroantimonate for 2h; Ambient temperature; further reagent: Ag2CO3; | 90% |
With silver nitrate | |
With zinc dibromide at 115℃; for 5h; Addition; Rearrangement; |
methyl 6-methoxy-2-naphthylacetate
carbonic acid dimethyl ester
A
methyl 2-methyl-2-phenylpropionate
B
methyl 2-(6-methoxy-2-naphthyl)propionate
Conditions | Yield |
---|---|
With potassium carbonate at 220℃; for 6h; | A n/a B 90% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; lithium dicyclohexylamide; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 18h; | 87% |
carbon dioxide
diazomethyl-trimethyl-silane
isopropenylbenzene
A
3-phenyl-butyric acid methyl ester
B
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; isopropenylbenzene With triethanolamine; tetraethylammonium iodide In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 3.5h; Electrochemical reaction; Stage #2: diazomethyl-trimethyl-silane In methanol; toluene for 0.666667h; regioselective reaction; | A 85% B n/a |
N-methoxy-2-methyl-2-phenylpropionamide
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 85℃; for 1.5h; Electrolysis; | 83% |
phenyl isopropyl ketone
trimethyl orthoformate
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With poly[4-(diacetoxyiodo)styrene]; sulfuric acid In acetonitrile at 60℃; for 0.5h; | 81% |
methyl 3-bromo-2-methyl-2-phenylpropanoate
A
3-phenyl-butyric acid methyl ester
B
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With titanium(IV) tetraethanolate; tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction (lead cathode, carbon rod anode, 4-5 F/mol); | A 80% B 5% |
carbonic acid dimethyl ester
benzeneacetic acid methyl ester
A
2-phenylpropionic acid methyl ester
B
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With potassium carbonate at 220℃; for 8h; | A 80% B n/a |
methanol
carbon monoxide
isopropenylbenzene
A
3-phenyl-butyric acid methyl ester
B
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With 5-chloro-2-hydroxybenzoic acid; boric acid; Tri(p-tolyl)phosphine; palladium diacetate under 31028.9 Torr; for 48h; Heating; | A 74% B n/a |
With trifluromethanesulfonate[bis(1-naphthyl)diphenylphosphine]palladium(II); toluene-4-sulfonic acid In 1,2-dichloro-ethane at 75℃; for 24h; Reagent/catalyst; Inert atmosphere; High pressure; chemoselective reaction; |
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; | 70% |
With aluminium trichloride |
2-(2-bromophenyl)-2-methylpropionaldehyde
butan-1-ol
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With 2BF4(1+)*C27H50P2*2H(1+); palladium diacetate; caesium carbonate In toluene at 60℃; for 14h; Inert atmosphere; | 70% |
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With sulfuric acid In methanol for 9h; Heating; | 68% |
dihydroxy-methyl-borane
2-methyl-2-phenylpropionic acid
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With pyridine; copper (II) carbonate hydroxide at 90℃; for 24h; Chan-Lam Coupling; | 65% |
methyl 2-dimethylbismuthanyl-2-methylpropanoate
iodobenzene
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
Stage #1: methyl 2-dimethylbismuthanyl-2-methylpropanoate In tetrahydrofuran at -78℃; for 0.5h; Stage #2: iodobenzene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h; | 48% |
methanol
phenyl isopropyl ketone
trimethyl orthoformate
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With iodine; silver nitrate for 5h; Heating; | 17% |
diazomethane
2-methyl-2-phenylpropionic acid
methyl 2-methyl-2-phenylpropionate
2-phenylpropionic acid methyl ester
methyl iodide
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
(i) NaNH2, liq. NH3, (ii) /BRN= 969135/; Multistep reaction; | |
With n-butyllithium; ammonium chloride; diisopropylamine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water | |
Stage #1: 2-phenylpropionic acid methyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; Schlenk technique; Inert atmosphere; |
methanol
2-bromo-2-methyl-1-phenyl-propan-1-one
A
2-methoxy-2-methyl-1-phenyl-1-propanone
B
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With zinc dibromide at 115℃; for 4h; |
methanol
2-methyl-2-phenylpropanoyl chloride
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
for 1h; Heating; Yield given; |
α,α,α',α'-teteramethyldibenzyl ketone
A
3-phenyl-butyric acid methyl ester
B
2-isopropylbenzoic acid
C
methyl 2-methyl-2-phenylpropionate
D
2-methyl-2,5-diphenyl-3-hexanone
E
2,6-diphenyl-4-heptanone
F
1-o-cumyl-3-phenyl-1-butanone
Conditions | Yield |
---|---|
With t-butoxide In tert-butyl alcohol at 185℃; Product distribution; |
phenylacetonitrile
carbonic acid dimethyl ester
A
methyl 2-methyl-2-phenylpropionate
B
1-phenylethyl cyanide
Conditions | Yield |
---|---|
With polyethylene glycol (PEG 6000); potassium carbonate at 180℃; Product distribution; Mechanism; further bases, solvents; |
methyl 3-bromo-2-methyl-2-phenylpropanoate
A
methyl 2-methyl-3-phenylpropionate
B
methyl 2-methyl-2-phenylpropionate
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 4h; Heating; Yield given. Yields of byproduct given; | |
With ammonium iodide; copper; zinc In methanol Product distribution; Ambient temperature; | A 30 % Spectr. B 60 % Spectr. |
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In benzene at 61℃; Product distribution; Kinetics; |
2-methyl-2,4-diphenyl-3-pentanone
A
3-phenyl-butyric acid methyl ester
B
2-isopropylbenzoic acid
C
2-phenylpropionic acid methyl ester
D
methyl 2-methyl-2-phenylpropionate
E
1-(2-Isopropyl-phenyl)-2-phenyl-propan-1-one
F
2,5-diphenyl-3-hexanone
Conditions | Yield |
---|---|
With t-butoxide In tert-butyl alcohol at 185℃; Product distribution; |
methyl 2-methyl-2-phenylpropionate
2-methyl-2-phenyl-propan-1-ol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; | 99% |
With sodium tetrahydroborate In tetrahydrofuran at 20℃; | 92% |
With lithium aluminium tetrahydride In diethyl ether at 0℃; |
methyl 2-methyl-2-phenylpropionate
2-methyl-2-phenyl propanoyl hydrazide
Conditions | Yield |
---|---|
With hydrazine hydrate for 6.5h; Heating; | 99% |
With hydrazine hydrate In methanol for 6h; Reflux; | 73% |
With hydrazine In ethanol for 6h; Reflux; | 73% |
methyl 2-methyl-2-phenylpropionate
2-methyl-2-phenylpropionic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In 1,4-dioxane for 24h; | 98% |
With sodium hydroxide In methanol; water for 4h; Ambient temperature; Yield given; | |
With sodium hydroxide; water In methanol at 80℃; for 12h; Hydrolysis; |
methyl 2-methyl-2-phenylpropionate
diisopropylamine
Conditions | Yield |
---|---|
at 20℃; | 92% |
methyl 2-methyl-2-phenylpropionate
acetyl chloride
Conditions | Yield |
---|---|
Stage #1: methyl 2-methyl-2-phenylpropionate With aluminum (III) chloride In carbon disulfide at 0 - 10℃; for 0.5h; Inert atmosphere; Stage #2: acetyl chloride In carbon disulfide at 0 - 40℃; for 21.3333h; Temperature; | 91.8% |
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran at 0 - 20℃; for 5h; | 89% |
methyl 2-methyl-2-phenylpropionate
methyl iodide
2,3-dimethyl-3-phenylbutan-2-ol
Conditions | Yield |
---|---|
magnesium In diethyl ether for 3h; Heating; | 81% |
methyl 2-methyl-2-phenylpropionate
dimethyl methane phosphonate
B
dimethyl 3-methyl-2-oxo-3-phenylbutylphosphonate
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane; water; ethyl acetate | A 75.7% B n/a |
methyl 2-methyl-2-phenylpropionate
dimethyl methane phosphonate
dimethyl 3-methyl-2-oxo-3-phenylbutylphosphonate
Conditions | Yield |
---|---|
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: methyl 2-methyl-2-phenylpropionate In tetrahydrofuran; hexane at -78℃; for 2.16667h; | 65% |
methyl 2-methyl-2-phenylpropionate
acrylic acid methyl ester
Conditions | Yield |
---|---|
With (S)-acetamidoalanine; palladium diacetate; silver nitrate at 80℃; for 24h; chemoselective reaction; | 65% |
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