[ CAS No. 73991-95-4 ] {[proInfo.proName]}

Name: 73991-95-4|(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid|95%
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Quality Control of [ 73991-95-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 73991-95-4 ]

SDS Specification

Alternatived Products of [ 73991-95-4 ]

Product Details of [ 73991-95-4 ]

CAS No. :	73991-95-4	MDL No. :	MFCD00211273
Formula :	C₇H₁₀O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IDQOCLIWDMZKBZ-BYPYZUCNSA-N
M.W :	174.15	Pubchem ID :	641720
Synonyms :

Safety of [ 73991-95-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 73991-95-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 73991-95-4 ]

[ 73991-95-4 ] Synthesis Path-Downstream 1~2

1
[ 636-61-3 ]
[ 77-76-9 ]
[ 73991-95-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	In toluene; for 2.5h;Heating / reflux;	Preparation 1 f(4R)-2,2-Dimethvl-5-oxo-1 ,3-dioxolan-4-vllacetic acid2,2-Dimethoxypropane (75mL, 610mmol) was added to,a suspension of D(+)malic acid (19.8g, 148mmol) in toluene (20OmL) and the mixture was heated under reflux for 2.5 hours. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with diethyl ether. The appropriate fractions were evaporated under reduced pressure and the residue was further purified by column chromatography on silica gel, eluting with heptane:diethyl ether, 66:33 to 50:50 to 0:100, to afford the title compound in 79% yield, 20.2g.1HNMR(400MHz, CDCI3) delta: 1.58(s, 3H), 1.63(s, 3H), 2.80-3.05(m, 2H), 4.70(m, 1 H)
79%	In toluene; for 2.5h;Heating / reflux;	Preparation 1; ff4R)-2.2-Diotamethyl-5-oxo-1,3-diotaoxolan-4-y)1acetiotac acid; 2,2-Diotamefhoxypropane (75mL, 610mmol) was added to a solution of D(+)maliotac acid (19 8g, 148mmol) in toluene (20OmL) and the mixture was heated under reflux for 2.5 hours. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with diethyl ether The appropriate fractions were evaporated under reduced pressure and the residue was further purified by column chromatography on silica gel, eluting with heptane diethyl ether, 66:33 to 50 50 to 0:100, to afford the title compound in 79% yield, 20.2g.1HNMR(400MHz, CDCI3) delta 1 58(S, 3H), 1 63(S, 3H), 2 80-3 05(m, 2H), 4 70(m, 1 H)
	With toluene-4-sulfonic acid; In dichloromethane; at 20℃; for 4h;	Step 1: [(4R)-2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid To a suspension of D-(+)-malic acid (10 g, 75 mmol) in CH2Cl2 (100 mL) was added 2,2-dimethoxypropane (23 g, 225 mmol) and p-toluenesulfonic acid (0.129 g, 0.75 mmol). The reaction mixture was stirred at rt for 4 h, filtered through silica gel (50% EtOAc/hexane) and concentrated to give the title compound. 1H NMR (300 MHz, CDCl3): delta9.70 (s, 1H), 4.69-4.73 (m, 1H), 2.97-3.04 (m, 1H), 2.81-2.89 (m, 1H), 1.62 (s, 3H), 1.57 (s, 3H).

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5313 - 5316
[2]Tetrahedron Letters,1987,vol. 28,p. 1685 - 1688
[3]Journal of Medicinal Chemistry,1998,vol. 41,p. 199 - 223
[4]Organic Letters,2012,vol. 14,p. 3648 - 3651
[5]Angewandte Chemie - International Edition,2011,vol. 50,p. 8739 - 8744
[6]Journal of Medicinal Chemistry,2008,vol. 51,p. 5387 - 5396
[7]Patent: WO2007/57767,2007,A2 .Location in patent: Page/Page column 30
[8]Patent: WO2007/57756,2007,A2 .Location in patent: Page/Page column 29
[9]Organic and Biomolecular Chemistry,2012,vol. 10,p. 5861 - 5872
[10]Tetrahedron Letters,1997,vol. 38,p. 4935 - 4938
[11]Patent: US2008/132542,2008,A1 .Location in patent: Page/Page column 30
[12]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9212 - 9216

2
[ 636-61-3 ]
[ 116-11-0 ]
[ 73991-95-4 ]

Yield	Reaction Conditions	Operation in experiment
50%	With pyridinium p-toluenesulfonate; In acetone; at 35℃; for 16h;	Preparation of (R)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid A solution of (R)-malic acid (4.50 g, 33.6 mmol), 2-methoxyprop-1-ene (9.68 g, 134 mmol) and pyridinium p-toluenesulfonate (844 mg, 3.36 mmol) in acetone (50 mL) was stirred at 35 C. for 16 h. After this time, water (200 mL) was added, and the aqueous solution was extracted with ethyl acetate (2*200 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/heptane to provide (R)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid (2.92 g, 50%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) delta 4.72 (dd, J=6.6, 3.9 Hz, 1H), 3.01 (dd, J=17.4, 3.9 Hz, 1H), 2.86 (dd, J=17.4, 6.6 Hz, 1H), 1.63 (s, 3H), 1.58 (s, 3H), CO2H proton not observed.

Reference： [1]Patent: US2016/326182,2016,A1 .Location in patent: Paragraph 0506; 0507

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Technical Information

• Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Acyl Group Substitution • Alcohols Convert Acyl Chlorides into Esters • Alcoholysis of Anhydrides • Amide Hydrolysis • Amide Hydrolysis • Amines Convert Esters into Amides • Anhydride Hydrolysis • Arndt-Eistert Homologation • Bouveault-Blanc Reduction • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Catalytic Hydrogenation • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Complex Metal Hydride Reductions • Convert Esters into Aldehydes Using a Milder Reducing Agent • Decarboxylation of 3-Ketoacids Yields Ketones • Decarboxylation of Substituted Propanedioic • Deprotection of Cbz-Amino Acids • Ester Cleavage • Ester Hydrolysis • Esters Hydrolyze to Carboxylic Acids and Alcohols • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Grignard Reagents Transform Esters into Alcohols • Hantzsch Pyridine Synthesis • Hunsdiecker-Borodin Reaction • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Nitriles Hydrolyze to Carboxylic Acids • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • The Conversion of Carboxylic Acids into Acyl Halides • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • Transesterification • Ugi Reaction

Historical Records

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[ 73991-95-4 ]

Esters

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Diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

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(2R,3R)-2,3-Diacetoxysuccinic acid

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[ 73991-95-4 ]

Dioxolanes

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Diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
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P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 73991-95-4 ] {[proInfo.proName]}

Quality Control of [ 73991-95-4 ]

Related Doc. of [ 73991-95-4 ]

Product Details of [ 73991-95-4 ]

Safety of [ 73991-95-4 ]

Application In Synthesis of [ 73991-95-4 ]

[ 73991-95-4 ] Synthesis Path-Downstream 1~2

Technical Information

Related Functional Groups of [ 73991-95-4 ]

Esters

Carboxylic Acids

Related Parent Nucleus of [ 73991-95-4 ]

Dioxolanes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 73991-95-4 ]

Related Parent Nucleus of
[ 73991-95-4 ]