Cyclobutanecarboxylic acid, 3-(hydroxymethyl)-2,2-dimethyl-, (1R,3S)- (9CI)

Base Information

• Chemical Name: Cyclobutanecarboxylic acid, 3-(hydroxymethyl)-2,2-dimethyl-, (1R,3S)- (9CI)
• CAS No.: 566190-42-9
• Molecular Formula: C8H14O3
• Molecular Weight: 158.19496
• Mol file: 566190-42-9.mol

Synonyms:Cyclobutanecarboxylic acid, 3-(hydroxymethyl)-2,2-dimethyl-, (1R,3S)- (9CI)

Chemical Property of Cyclobutanecarboxylic acid, 3-(hydroxymethyl)-2,2-dimethyl-, (1R,3S)- (9CI)

Chemical Property:

• Boiling Point: 282.3±13.0 °C(Predicted)
• PKA: 4.71±0.60(Predicted)
• PSA: 57.53000
• Density: 1.128±0.06 g/cm3(Predicted)
• LogP: 0.72560

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclobutanecarboxylic acid, 3-(hydroxymethyl)-2,2-dimethyl-, (1R,3S)- (9CI)

There total 11 articles about Cyclobutanecarboxylic acid, 3-(hydroxymethyl)-2,2-dimethyl-, (1R,3S)- (9CI) 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: 61.0%

(1R,3S)-3-hydroxymethyl-2,2-dimethylcyclobutyl methyl ketone (528560-17-0,129940-75-6) → cis-2.2-Dimethyl-3-hydroxymethyl-1-carboxy-cyclobutan (90113-35-2,566190-42-9)

Guidance literature:

With sodium hypobromide; In 1,4-dioxane; at 0 - 20 ℃; for 7h;

DOI:10.1016/S0957-4166(02)00749-8

Reference yield:

(1S,3R)-3-(2-methyl-1,3-dioxolan-2-yl)-2,2-dimethylcyclobutylmethanol (288848-33-9) → cis-2.2-Dimethyl-3-hydroxymethyl-1-carboxy-cyclobutan (90113-35-2,566190-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridinium p-toluenesulfonate; H₂O / acetone / 5 h / Heating

2: 61 percent / aq. NaOBr / dioxane / 7 h / 0 - 20 °C

With sodium hypobromide; water; pyridinium p-toluenesulfonate; In 1,4-dioxane; acetone; 2: Lieben degradation;

DOI:10.1016/S0957-4166(02)00749-8

Reference yield:

→ 2.2-Dimethyl-3-hydroxymethyl-1-carboxy-cyclobutan (90113-35-2,566190-42-9)

Guidance literature:

With ethanol; sodium;

upstream raw materials:

(1R,3S)-3-hydroxymethyl-2,2-dimethylcyclobutyl methyl ketone

(1S,3R)-3-(2-methyl-1,3-dioxolan-2-yl)-2,2-dimethylcyclobutylmethanol

(+/-)-3c-iodomethyl-2,2-dimethyl-cyclobutane-r-carboxylic acid methyl ester

(+/-)-3c-hydroxymethyl-2,2-dimethyl-cyclobutane-r-carboxylic acid methyl ester