ChemicalBook CAS DataBase List GLYOXAL DIMETHYL ACETAL

GLYOXAL DIMETHYL ACETAL synthesis

9synthesis methods

Product Name:GLYOXAL DIMETHYL ACETAL
CAS Number:51673-84-8
Molecular formula:C4H8O3
Molecular Weight:104.1

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51673-84-8
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Yield:51673-84-8 350 mg

Reaction Conditions:

with ruthenium trichloride in dichloromethane;acetonitrile at 20; for 0.5 h;

Steps:

4.2.8. Dimethoxyacetaldehyde 10
To a suspension of NaIO₄ (3 g, 14 mmol) supported on silica (10 g) in DCM (30 mL) was added alkene 9 (355 mg, 2 mmol) previously diluted in DCM (20 mL). The mixture was stirred for 30 min at room temperature before being filtered. The solid residue was washed twice with DCM (20 mL). The organic phase was dried over MgSO₄, filtered and concentrated under vacuum very carefully (20 ^oC, 300 mmHg) due to the high volatility of aldehyde 10. The residue was a clear liquid (350 mg, 85% crude) used in the next step without further purification. ¹H NMR (400 MHz, CDCl₃): δ = 9.47 (d, J = 1.5 Hz, 1H, 1-H), 4.50 (d, J = 1.5 Hz, 1H, 2-H), 3.46 (s, 6H, 3-H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 199.2 (1-C), 122.3 (2-C), 54.6 (3-C) ppm.

References:

Camps Bres, Flora;Guerard-Helaine, Christine;Fernandes, Carlos;Castillo, Jose A.;Lemaire, Marielle [Tetrahedron Asymmetry,2013,vol. 24,# 18,p. 1175 - 1181]

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