2,2-Dimethyl-3-oxocyclobutanecarboxylic acid

Base Information

• Chemical Name: 2,2-Dimethyl-3-oxocyclobutanecarboxylic acid
• CAS No.: 3183-43-5
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.155
• Hs Code.: 2916200090
• NSC Number: 123321
• DSSTox Substance ID: DTXSID70298457
• Mol file: 3183-43-5.mol

Synonyms:2,2-dimethyl-3-oxocyclobutanecarboxylic acid;3183-43-5;2,2-dimethyl-3-oxocyclobutane-1-carboxylic acid;NSC123321;Cyclobutanecarboxylicacid, 2,2-dimethyl-3-oxo-;SCHEMBL16822071;DTXSID70298457;MGZMYBGVLXPPOG-UHFFFAOYSA-N;MFCD23106160;AKOS025291195;NSC-123321;PB39064;SB20948;AS-34770;2,2-dimethyl-3-oxocyclobutanecarboxylicacid;CS-0052187;EN300-221687;2,2-dimethyl-3-oxo-cyclobutane-1-carboxylic acid;A875796

Chemical Property of 2,2-Dimethyl-3-oxocyclobutanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0.00203mmHg at 25°C
• Boiling Point: 269.6°C at 760 mmHg
• Flash Point: 131.1°C
• PSA: 54.37000
• Density: 1.203g/cm³
• LogP: 0.68620
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 193

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,2-Dimethyl-3-oxocyclobutanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(CC1=O)C(=O)O)C

Technology Process of 2,2-Dimethyl-3-oxocyclobutanecarboxylic acid

There total 1 articles about 2,2-Dimethyl-3-oxocyclobutanecarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

2,2-dimethyl-3-oxo-cyclobutanecarboxylic acid methyl ester (78685-51-5,527751-17-3) → 2,2-dimethyl-3-oxocyclobutanecarboxylic acid (3183-43-5)

Guidance literature:

2,2-dimethyl-3-oxo-cyclobutanecarboxylic acid methyl ester; With water; lithium hydroxide; In tetrahydrofuran; at 23 ℃; for 18h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

DOI:10.1021/jo102257k

Reference yield: 16.0%

2,2-dimethyl-3-oxocyclobutanecarboxylic acid (3183-43-5) + tert-butyl alcohol (75-65-0) → tert-butyl (2,2-dimethyl-3-oxocyclobutyl)carbamate (1434141-90-8)

Guidance literature:

2,2-dimethyl-3-oxocyclobutanecarboxylic acid; With diphenyl phosphoryl azide; triethylamine; In toluene; at 0 - 100 ℃; for 4h; Reflux;

tert-butyl alcohol; In toluene; for 15h; Temperature; Reflux;

Reference yield:

2,2-dimethyl-3-oxocyclobutanecarboxylic acid (3183-43-5) → C24H31ClN6O2

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; diphenyl phosphoryl azide / toluene / 4 h / 0 - 100 °C / Reflux

1.2: 15 h / Reflux

2.1: hydroxylamine hydrochloride; sodium carbonate / water; methanol / 20 °C

3.1: ammonia; hydrogen / methanol / 20 °C

4.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / 125 °C / Microwave irradiation

With diphenyl phosphoryl azide; hydroxylamine hydrochloride; ammonia; hydrogen; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; water; toluene;

upstream raw materials:

2,2-dimethyl-3-oxo-cyclobutanecarboxylic acid methyl ester

Downstream raw materials:

tert-butyl (3-hydroxy-2,2-dimethylcyclobutyl)carbamate

3-amino-2,2-dimethylcyclobutanol

tert-butyl (3-amino-2,2-dimethylcyclobutyl)carbamate

tert-butyl (2,2-dimethyl-3-oxocyclobutyl)carbamate

Refernces

• 1、 O'Brien, Jeannette M.,Kingsbury, Jason S.. "A Practical synthesis of 3-Acyl cyclobutanones by [2 〈 2] annulation. Mechanism and utility of the zn(II)-Catalyzed condensation of r-Chloroenamines with electron-deficient alkenes". experimental part. p. 1662 - 1672. Retrieved 2011/05/12.