5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Base Information

• Chemical Name: 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS No.: 85920-63-4
• Molecular Formula: C8H10O5
• Molecular Weight: 186.164
• Hs Code.: 2934999090
• Mol file: 85920-63-4.mol

Synonyms:acetyl Meldrum's salt;;acetyl-Meldrum's acid;;

Chemical Property of 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Chemical Property:

• Melting Point: 83-84 °C
• Boiling Point: 385.9±42.0 °C(Predicted)
• PKA: 4.50±1.00(Predicted)
• PSA: 72.83000
• Density: 1.303
• LogP: 0.65450
• Storage Temp.: 2-8°C

Purity/Quality:

98%, ^*data from raw suppliers

5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Acetyl Meldrum''s Acid is used in preparation of Bicyclic β-Lactams/Oxazinones via Cycloaddition and metathesis starting from Acyl/Carbamoyl-dimethyl-dioxa-diones.

Technology Process of 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

There total 6 articles about 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 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: 99.0%

cycl-isopropylidene malonate (2033-24-1) + acetyl chloride (75-36-5) → 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (85920-63-4)

Guidance literature:

With dmap; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201905482

Reference yield: 62.0%

cycl-isopropylidene malonate (2033-24-1) → 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (85920-63-4)

Guidance literature:

With pyridine;

DOI:10.1080/10426507.2012.668988

Reference yield: 60.0%

cycl-isopropylidene malonate (2033-24-1) + Triethyl orthoacetate (78-39-7) → 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (85920-63-4)

Guidance literature:

cycl-isopropylidene malonate; Triethyl orthoacetate; In dichloromethane; for 120h; Heating;

With water; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1002/jhet.5570430217

upstream raw materials:

cycl-isopropylidene malonate

acetyl chloride

Triethyl orthoacetate

2,2-dimethyl-5-[1-(methylthio)ethylidene]-1,3-dioxane-4,6-dione

Downstream raw materials:

(9'-Bromo-1'-nonyl)-3-oxobutanoate

trans-α-phenylcinnamyl acetoacetate

cis-α-phenylcinnamyl acetoacetate

3-Oxo-butyric acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester

Refernces

• 1、 Bodenschatz, Kevin,St?ckl, Julia,Winterer, Markus,Schobert, Rainer. "A synthetic approach to 5/5/6-polycyclic tetramate macrolactams of the discodermide type". . . Retrieved 2021/05/31.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF 4-({(1 R)-2-[5-(2-FLUORO-3METHOXYPHENYL)-3-{[2-FLUORO-6-(TRIFLUORO METHYL) PHENYL]METHYL}-4-METHYL-2,6-DIOXO-3,6DIHYDROPYRIMIDIN-1(2 H)-YL]-1-PHENYLETHYL}AMINO)BUTANOIC ACID OR ITS PHARMACEUTICALLY ACCEPTABLE SALTS". Page/Page column 17. . Retrieved 2021/07/02.