ChemicalBook > Product Catalog >Pharmaceutical intermediates >4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one Structure
CAS No.
91526-18-0
Chemical Name:
4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one
Synonyms
DMDO-OH;4-(HydroxyMethyl)-5-Methyl-[1,3]dioxol-2-one;AZATMint-D;Azilsartan Impurity 55;Azilasartan medoximil(HPLC-98.2%);4-(hidroximetil)-5-metil-1,3-dioxol-2-ona;4-(hidroxiMetil)-5-Metil-1,3-dioxol-2-one;4-(hydroxymethyl)-5-methyl-l,3-dioxol-2-one;4-(hydroxymethyl)-5-methyl-1,3-Diaxole-2-one;1,3-Dioxol-2-one, 4-(hydroxymethyl)-5-methyl-
CBNumber:
CB82515847
Molecular Formula:
C5H6O4
Molecular Weight:
130.1
MOL File:
91526-18-0.mol
Modify Date:
2024/8/7 19:09:42

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one Properties

Boiling point 214℃
Density 1.367
Flash point 93℃
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility Chloroform (Slightly), Methanol (Slightly)
form liquid
pka 14.54±0.10(Predicted)
color Pale yellow
InChI InChI=1S/C5H6O4/c1-3-4(2-6)9-5(7)8-3/h6H,2H2,1H3
InChIKey JEQSUJXHFAXJOW-UHFFFAOYSA-N
SMILES O1C(C)=C(CO)OC1=O

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501
HS Code  2932990090

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one Chemical Properties,Uses,Production

Description

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one is a reagent used in organic synthesis, particularly for the introduction of the non-chiral (oxodioxolenyl)methyl carbamate group to active pharmaceutical ingredients (APIs) to afford the corresponding pro-drug.

Definition

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one can be reacted with oxalyl chloride to afford (5-methyl-2-oxo-1,3-dioxol-4-yl) methylglyoxal chloride, which provides for an alternative approach to introduce the (oxodioxolenyl) methylcarbamate group.

Uses

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one is used in preparation method of key intermediate of olmesartan medoxomil.

Preparation

At 20-25°C, 50 g of 4-chloromethyl-5-methyl-1,3-dioxol-2-one and 45 g of formic acid were added to 500 mL of acetonitrile. The reaction was cooled to 10-15°C followed by 95 g of triethylamine added. The mixture was heated to 60-65°C and stirred for approximately 5-6 h. The reaction system was subsequently cooled to 15-20°C, filtered, and washed with acetonitrile. Collecting filtrate, and the acetonitrile was removed under vacuum to concentrate the solution. The reaction system was again cooled to 25-30°C, and ethyl acetate and water were added. The mixture was then stirred for approximately 15-20 minutes at 25-30°C. Finally, 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one was obtained after further purification.

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1,3-Dioxol-2-one, 4-(hydroxymethyl)-5-methyl- 4-(hidroximetil)-5-metil-1,3-dioxol-2-ona 4-(hydroxymethyl)-5-methyl-l,3-dioxol-2-one 4-(hidroxiMetil)-5-Metil-1,3-dioxol-2-one 4-Methyl-5-hydroxyMethyl-2-oxo-1,3-dioxol-4-ene AZATMint-D 4-(hidroximetil)-5-metil-1,3-dioxol-2-ona ISO 9001:2015 REACH Azilsartan Impurity 55 Azilasartan medoximil(HPLC-98.2%) 4-(hydroxymethyl)-5-methyl-2H-1,3-dioxol-2-one 4-(HydroxyMethyl)-5-Methyl-[1,3]dioxol-2-one DMDO-OH 4- (hydroxymethyl) -5- methyl -[1,3] dioxolane -2- one 4-(hydroxymethyl)-5-methyl-1,3-Diaxole-2-one 91526-18-0 94526-18-0