57625-74-8

Basic information

• Product Name: Methyl 2,2-dimethylphenylacetate
• Synonyms: Methyl 2,2-dimethylphenylacetate, >=98%;alpha,alpha-dimethylphenyl-acetic acid methyl ester;a,a-Dimethylphenylmethylacetate;alpha,alpha-Dimethyl Benzeneacetic Acid Methyl Ester;ALPHA,ALPHA-DIMETHYLPHENYLMETHYLACETATE;Methyl 2,2-dimethylphenylacetate;Methyl 2-methyl-2-phenylpropanoate;Methyl dimethylbenzeneacetate
• CAS NO: 57625-74-8
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• EINECS: 1312995-182-4
• Mol File: 57625-74-8.mol
• Article Data: 55

Chemical Properties

• Boiling Point: 230.2°C at 760 mmHg
• Flash Point: 92.2°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 0.0666mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Methyl 2,2-dimethylphenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,2-dimethylphenylacetate(57625-74-8)
• EPA Substance Registry System: Methyl 2,2-dimethylphenylacetate(57625-74-8)

Safety Data

• Hazardous Substances Data: 57625-74-8(Hazardous Substances Data)

Usage

Uses

Methyl Dimethylbenzeneacetate (cas# 57625-74-8) is a compound useful in organic synthesis.

InChI:InChI=1/C11H14O2/c1-11(2,10(12)13-3)9-7-5-4-6-8-9/h4-8H,1-3H3

Synthetic route

methanol (67-56-1) + 2-methyl-2-phenylpropionic acid (826-55-1) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (101-41-7) + methyl iodide (74-88-4) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

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%

Methyl isobutyrate (547-63-7) + chlorobenzene (108-90-7) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (811-98-3) + 2-(2-bromophenyl)-2-methylpropionaldehyde (212626-89-6) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With 2BF4(1+)*C27H50P2*2H(1+); palladium diacetate; caesium carbonate In toluene at 60℃; for 14h; Inert atmosphere;	92%

bromobenzene (108-86-1) + 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene (31469-15-5) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (67-56-1) + 2-(2-bromophenyl)-2-methylpropionaldehyde (212626-89-6) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (826-55-1) + carbonic acid dimethyl ester (616-38-6) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry;	91%

methanol (67-56-1) + 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (23981-48-8) + carbonic acid dimethyl ester (616-38-6) → methyl 2-methyl-2-phenylpropionate (57625-74-8) + methyl 2-(6-methoxy-2-naphthyl)propionate (30012-51-2)

Conditions	Yield
With potassium carbonate at 220℃; for 6h;	A n/a B 90%

bromobenzene (108-86-1) + Methyl isobutyrate (547-63-7) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With tri-tert-butyl phosphine; lithium dicyclohexylamide; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 18h;	87%

carbon dioxide (124-38-9) + diazomethyl-trimethyl-silane (18107-18-1) + isopropenylbenzene (98-83-9) → 3-phenyl-butyric acid methyl ester (3461-39-0) + methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (1072809-89-2) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 85℃; for 1.5h; Electrolysis;	83%

phenyl isopropyl ketone (611-70-1) + trimethyl orthoformate (149-73-5) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With poly[4-(diacetoxyiodo)styrene]; sulfuric acid In acetonitrile at 60℃; for 0.5h;	81%

methyl 3-bromo-2-methyl-2-phenylpropanoate (84782-16-1) → 3-phenyl-butyric acid methyl ester (3461-39-0) + methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (616-38-6) + benzeneacetic acid methyl ester (101-41-7) → 2-phenylpropionic acid methyl ester (31508-44-8) + methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With potassium carbonate at 220℃; for 8h;	A 80% B n/a

methanol (67-56-1) + carbon monoxide (201230-82-2) + isopropenylbenzene (98-83-9) → 3-phenyl-butyric acid methyl ester (3461-39-0) + methyl 2-methyl-2-phenylpropionate (57625-74-8)

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;

methacrylic acid methyl ester (80-62-6) + benzene (71-43-2) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃;	70%
With aluminium trichloride

2-(2-bromophenyl)-2-methylpropionaldehyde (212626-89-6) + butan-1-ol (71-36-3) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With 2BF4(1+)*C27H50P2*2H(1+); palladium diacetate; caesium carbonate In toluene at 60℃; for 14h; Inert atmosphere;	70%

N-[1-Methoxy-2-methyl-2-phenyl-prop-(Z)-ylidene]-4-methyl-benzenesulfonamide → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With sulfuric acid In methanol for 9h; Heating;	68%

dihydroxy-methyl-borane (13061-96-6) + 2-methyl-2-phenylpropionic acid (826-55-1) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With pyridine; copper (II) carbonate hydroxide at 90℃; for 24h; Chan-Lam Coupling;	65%

methyl 2-dimethylbismuthanyl-2-methylpropanoate (934733-52-5) + iodobenzene (591-50-4) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (67-56-1) + phenyl isopropyl ketone (611-70-1) + trimethyl orthoformate (149-73-5) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With iodine; silver nitrate for 5h; Heating;	17%

diazomethane (186581-53-3, 908094-01-9) + 2-methyl-2-phenylpropionic acid (826-55-1) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

2-phenylpropionic acid methyl ester (31508-44-8) + methyl iodide (74-88-4) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (67-56-1) + 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) → 2-methoxy-2-methyl-1-phenyl-1-propanone (59671-36-2) + methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With zinc dibromide at 115℃; for 4h;

methanol (67-56-1) + 2-methyl-2-phenylpropanoyl chloride (36293-05-7) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
for 1h; Heating; Yield given;

α,α,α',α'-teteramethyldibenzyl ketone (71254-82-5) → 3-phenyl-butyric acid methyl ester (3461-39-0) + 2-isopropylbenzoic acid (2438-04-2) + methyl 2-methyl-2-phenylpropionate (57625-74-8) + 2-methyl-2,5-diphenyl-3-hexanone (71302-96-0) + 2,6-diphenyl-4-heptanone (66164-33-8) + 1-o-cumyl-3-phenyl-1-butanone (129976-23-4)

Conditions	Yield
With t-butoxide In tert-butyl alcohol at 185℃; Product distribution;

phenylacetonitrile (140-29-4) + carbonic acid dimethyl ester (616-38-6) → methyl 2-methyl-2-phenylpropionate (57625-74-8) + 1-phenylethyl cyanide (1823-91-2)

Conditions	Yield
With polyethylene glycol (PEG 6000); potassium carbonate at 180℃; Product distribution; Mechanism; further bases, solvents;

methyl 3-bromo-2-methyl-2-phenylpropanoate (84782-16-1) → methyl 2-methyl-3-phenylpropionate (29393-16-6, 38574-62-8, 78964-60-0, 29417-83-2) + methyl 2-methyl-2-phenylpropionate (57625-74-8)

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 (71254-83-6) → 3-phenyl-butyric acid methyl ester (3461-39-0) + 2-isopropylbenzoic acid (2438-04-2) + 2-phenylpropionic acid methyl ester (31508-44-8) + methyl 2-methyl-2-phenylpropionate (57625-74-8) + 1-(2-Isopropyl-phenyl)-2-phenyl-propan-1-one (71254-87-0) + 2,5-diphenyl-3-hexanone (71254-85-8, 71254-86-9)

Conditions	Yield
With t-butoxide In tert-butyl alcohol at 185℃; Product distribution;

methyl 2-methyl-2-phenylpropionate (57625-74-8) → 2-methyl-2-phenyl-propan-1-ol (2173-69-5)

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 (57625-74-8) → 2-methyl-2-phenyl propanoyl hydrazide (5809-15-4)

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 (57625-74-8) → 2-methyl-2-phenylpropionic acid (826-55-1)

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 (57625-74-8) + diisopropylamine (108-18-9) → α,α-dimethylphenylacetyldiisopropylamine

Conditions	Yield
at 20℃;	92%

methyl 2-methyl-2-phenylpropionate (57625-74-8) + acetyl chloride (75-36-5) → methyl 2-(4-acetylphenyl)isobutyrate

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%

1,5-dibromo-pentane (111-24-0) + methyl 2-methyl-2-phenylpropionate (57625-74-8) → C15H22O

Conditions	Yield
With magnesium In tetrahydrofuran at 0 - 20℃; for 5h;	89%

methyl 2-methyl-2-phenylpropionate (57625-74-8) + methyl iodide (74-88-4) → 2,3-dimethyl-3-phenylbutan-2-ol (2371-91-7)

Conditions	Yield
magnesium In diethyl ether for 3h; Heating;	81%

methyl 2-methyl-2-phenylpropionate (57625-74-8) + dimethyl methane phosphonate (756-79-6) → dimethyl 3-methyl-2-oxo-3-phenylbuthylphosphonate + dimethyl 3-methyl-2-oxo-3-phenylbutylphosphonate (87929-30-4)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane; water; ethyl acetate	A 75.7% B n/a

methyl 2-methyl-2-phenylpropionate (57625-74-8) + dimethyl methane phosphonate (756-79-6) → dimethyl 3-methyl-2-oxo-3-phenylbutylphosphonate (87929-30-4)

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 (57625-74-8) + acrylic acid methyl ester (292638-85-8) → (E)-methyl 3-(2-(1-methoxy-2-methyl-1-oxopropan-2-yl)phenyl)acrylate

Conditions	Yield
With (S)-acetamidoalanine; palladium diacetate; silver nitrate at 80℃; for 24h; chemoselective reaction;	65%

Upstream product

• 101-41-7 benzeneacetic acid methyl ester 
• 74-88-4 methyl iodide 
• 108-86-1 bromobenzene 
• 547-63-7 Methyl isobutyrate 
• 74-87-3 methylene chloride 
• 826-55-1 2-methyl-2-phenylpropionic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 177748-63-9 methyl 2-(2-bromophenyl)-2-methylpropanoate 
• 1072809-89-2 N-methoxy-2-methyl-2-phenylpropionamide 
• 10409-54-8 2-bromo-2-methyl-1-phenyl-propan-1-one 
• 13694-96-7 2-methoxy-3,3-dimethyl-2-phenyl-oxirane 
• 13061-96-6 dihydroxy-methyl-borane 
• 75-75-2 methanesulfonic acid 
• 1195-98-8 2-methyl-2-phenylpropionitrile 

Downstream Products

• 87929-30-4 dimethyl 3-methyl-2-oxo-3-phenylbutylphosphonate 
• 84542-11-0 2-(4-formylphenyl)-2-methylpropionic acid methyl ester 
• 1016447-97-4 2-methyl-2-phenyl-N-(pyridin-2-ylmethyl)propanamide 
• 253688-62-9 Ro 64-1056 
• 91496-72-9 2-(2-acetylphenyl)-2,2-dimethylacetic acid 
• 857768-18-4 2-(4-acetyl-phenyl)-2-methyl-propionic acid 
• 1256584-73-2 2-(4-ethyl-3-iodophenyl)-2-methylpropanoic acid 
• 1247119-83-0 2-(4-ethylphenyl)-2-methyl-propanoic acid 
• 1256584-72-1 2-(4-Vinylphenyl)-2-methylpropanoic acid 
• 1394117-23-7 methyl α,α-dimethyl-4-(2-bromoethyl)phenylacetate 
• 2371-91-7 2,3-dimethyl-3-phenylbutan-2-ol 
• 1327475-16-0 2-methyl-2-phenyl-N-(quinolin-8-yl)propanamide 

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