Abstract
The versatile reagent chloromethyl methyl ether (MOM-Cl) is synthesized by using inexpensive starting materials in a large scale. A modification of the existing methods reduces material costs by more than 80%.
Key words
protecting group - MOM-Cl - alcohols - phenols - acetals
References
1 Greene TW.
Wuts PGM.
Protective Groups in Organic Synthesis
3rd ed:
John Wiley and Sons;
Weinheim:
1999.
2a Amato JS.
Karady M.
Sletzinger M.
Weinstock LM.
J. Org. Chem.
1994,
59:
6499
2b Linderman RJ.
Jaber M.
Griedel BD.
J. Org. Chem.
1994,
59:
6499
2c Chong JM.
Shen L.
Synth. Commun.
1998,
28:
2801
3 Material costs are calculated from the prices quoted in the Aldrich Chemical Co. catalog (2003). For comparison, one mole of chloromethyl methyl ether costs 229 US $. A commercial sample of chloromethyl methyl ether contained about 4% of bis(chloromethyl)ether.
4 To ensure gas tightness, PTFE-sleeves were used on all glass connections.
5 All reagents were purchased by common suppliers and used as received without any further purification.
6 The integrals of the product signals (δ = 3.52 and 5.46 ppm) are compared with those of dimethoxymethane (δ = 3.34 and 4.56 ppm).
7 Without further purification, the product contains about 1% dimethoxymethane (1 H NMR, δ = 3.34 and 4.56 ppm). This is sufficient for most applications. The content of bis(chloromethyl)ether was found to be less than 0.1% (GC, conditions 50 m × 0.32 mm FS-SE-52-CB-0.25 fused silica column, column temperature 60 °C, injector temperature 240 °C, detector temperature (FID), nitrogen flow 1 mL/min tR (MOM-Cl) = 5.79 min, tR [bis(chloromethyl)ether] = 7.97 min.
