Ethanone, 1-[4-(hydroxymethyl)-2-cyclobuten-1-yl]-, cis- (9CI)

Base Information

• Chemical Name: Ethanone, 1-[4-(hydroxymethyl)-2-cyclobuten-1-yl]-, cis- (9CI)
• CAS No.: 174712-74-4
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.155
• Mol file: 174712-74-4.mol

Synonyms:Ethanone, 1-[4-(hydroxymethyl)-2-cyclobuten-1-yl]-, cis- (9CI)

Chemical Property of Ethanone, 1-[4-(hydroxymethyl)-2-cyclobuten-1-yl]-, cis- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethanone, 1-[4-(hydroxymethyl)-2-cyclobuten-1-yl]-, cis- (9CI)

There total 12 articles about Ethanone, 1-[4-(hydroxymethyl)-2-cyclobuten-1-yl]-, cis- (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:

cyclobut-3-ene-1,2-dicarboxylic acid anhydride (10374-07-9) → cis-4-(1-oxoethyl)-2-cyclobutene-1-methanol (174712-74-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 15 percent / LiAlH₄ / tetrahydrofuran / 48 h / Heating

2: 67 percent / PCC, Celite 521 / CH₂Cl₂ / 14 h / Ambient temperature

3: 1.) Me₃Al / 1.) CH₂Cl₂, 0 deg C, 20 min, 2.) CH₂Cl₂, 1 h

4: 79 percent / imidazole / dimethylformamide; tetrahydrofuran / 3 h / Ambient temperature

5: 86 percent / tetrahydrofuran; toluene / 3 h / Ambient temperature

6: aq. HF / acetonitrile / 1 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; Celite; hydrogen fluoride; trimethylaluminum; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/0040-4020(96)00039-7

Reference yield:

(1R,4S)-(4-hydroxymethylcyclobut-2-enyl)methanol (77774-01-7,446840-28-4) → cis-4-(1-oxoethyl)-2-cyclobutene-1-methanol (174712-74-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 67 percent / PCC, Celite 521 / CH₂Cl₂ / 14 h / Ambient temperature

2: 1.) Me₃Al / 1.) CH₂Cl₂, 0 deg C, 20 min, 2.) CH₂Cl₂, 1 h

3: 79 percent / imidazole / dimethylformamide; tetrahydrofuran / 3 h / Ambient temperature

4: 86 percent / tetrahydrofuran; toluene / 3 h / Ambient temperature

5: aq. HF / acetonitrile / 1 h / Ambient temperature

With 1H-imidazole; Celite; hydrogen fluoride; trimethylaluminum; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/0040-4020(96)00039-7

Reference yield:

cis-Cyclobut-1-en-3,4-dicarbonsaeure (27652-29-5) → cis-4-(1-oxoethyl)-2-cyclobutene-1-methanol (174712-74-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaBH₄, CaCl₂, 1M KOH, 2.) 2M HCl / 1.) ethanol, 6 h, 2.) ethanol, 12 h

2: 1.) Me₃Al / 1.) CH₂Cl₂, 0 deg C, 20 min, 2.) CH₂Cl₂, 1 h

3: 79 percent / imidazole / dimethylformamide; tetrahydrofuran / 3 h / Ambient temperature

4: 86 percent / tetrahydrofuran; toluene / 3 h / Ambient temperature

5: aq. HF / acetonitrile / 1 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; hydrogen fluoride; trimethylaluminum; calcium chloride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/0040-4020(96)00039-7

upstream raw materials:

cyclobut-3-ene-1,2-dicarboxylic acid anhydride

(1R,4S)-(4-hydroxymethylcyclobut-2-enyl)methanol

cis-Cyclobut-1-en-3,4-dicarbonsaeure

cis-3-cyclobutene-1,2-dicarboxylic acid monomethyl ester