Preparation of Chloromethyl Methyl Ether Revisited

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• When the Linderman procedure was published the cost per mole (Aldrich Chemical Co. 1994–95 catalog prices) of the C6 and C8 acid chlorides was $17.82 and $13.44, respectively. Since then, the price (Aldrich, 1996–97) for the C8 acid chloride has remained unchanged but the C6 acid chloride price has increased to $38.36/mol
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• The 1H NMR spectrum of MOMCl shows 2 sharp singlets with clearly visible 13C satellites (0.55% each). When the amplitude of the spectrum was increased so that these 13C satellites were 5 cm high (with signal/noise > 20), the signals for MeOCH2OMe and (ClCH2)2O were not visible. A commercial (Aldrich Chemical Co.) sample of MOMCl showed a signal at δ 5.56, which may be attributed to (ClCH2)2O, of comparable intensity to the 13C satellites
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• For comparison, the material cost (Aldrich Chemical Co. 1996–97 catalog prices, US$) of different routes to one mole of MOMCl are: purchase = $158.16; hexanoyl chloride + dimethoxymethane = $39.98; (hexanoic acid + thionyl chloride) + dimethoxymethane = $8.59; decanoyl chloride + dimethoxymethane = $6.03.
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