Chloromethyl Methyl Ether → HCID 59649720, compound

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Reaction Steps

N,N-Diisopropylethylamine (5.3 mL, 30.5 mmol) (Aldrich) was added to a suspension of ethyl 3-hydroxy-4-methylbenzoate (5.0 g, 27.75 mmol) (from Example 2 supra) in dichloromethane (20 mL) with cooling in an ice-water bath. Chloromethylmethyl ether (4.2 mL, 55.5 mmol) (Aldrich) was then added dropwise and the mixture stirred at room temperature for 5 hours. The mixture was then diluted with ether (100 mL) and washed with mixture of water (100 mL), followed by 0.1 N HCl (2×100 mL) and brine (100 mL). Aqueous layers were back washed with ether (100 mL). Organic solutions were combined, dried (MgSO4), filtered and concentrated. Residue was filtered through silica gel (Biotage 40 L) eluting with dichloromethane. Fractions were combined and concentrated to give 3-methoxymethoxy-4-methyl-benzoic acid ethyl ester as colorless oil. (Yield 4.88 g, 78.4%).

Provenance & Evidence