Chloromethyl Methyl Ether → HCID 131725674, compound

To a solution of 4-hydroxyphthalic acid (0.45 g, 2.47 mmol) in anhydrous N,N-dimethylformamide (5 ml) under nitrogen was added chloromethyl methyl ether (1.13 ml, 14.8 mmol) and diisopropylethylamine (2.6 ml, 14.8 mmol). The reaction was stirred at ambient temperature for 18 h. and then concentrated in vacuo. The crude material was partitioned between ethyl acetate (50 ml) and water (15 ml). The layers were separated, the organic layer washed with water (3×10 ml), brine (2×10 ml), dried (Na2SO4), filtered and the solvent evaporated in vacuo. The resulting oil was dissolved in ethanol (5 ml) and sodium hydroxide (0.12 g, 7.4 mmol) dissolved in water (1 ml) was added to the reaction. The solution was stirred at ambient temperature for 48 h. and then concentrated in vacuo affording 4-methoxymethoxy-phthalic acid di-sodium salt which was used without purification.

1. concentrationconcentrated in vacuo
2. customThe crude material was partitioned between ethyl acetate (50 ml) and water (15 ml)
3. customThe layers were separated
4. washthe organic layer washed with water (3×10 ml), brine (2×10 ml)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customthe solvent evaporated in vacuo
8. dissolutionThe resulting oil was dissolved in ethanol (5 ml)
9. additionwas added to the reaction
10. stirringThe solution was stirred at ambient temperature for 48 h.
11. concentrationconcentrated in vacuo

ORD record

ord-e9223611a48540468797266c221e47f7

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115624B1