Chloromethyl Methyl Ether → 3-(Methoxymethoxy)-4-methylbenzoic acid

In a similar manner to Step 1 of Example 347, 3-hydroxy-4-methylbenzoic acid (2.00 g, 13.1 mmol) was suspended in dichloromethane (50 mL), and the suspension was treated with diisopropylethylamine (13.7 mL, 78.6 mmol) and chloromethyl methyl ether (5.00 mL, 65.8 mmol). The solvent was evaporated under reduced pressure. The residue was dissolved in methanol (50 mL), and the solution was treated with 2 mol/L aqueous potassium hydroxide solution (50 mL). The solvent was evaporated under reduced pressure. The residue was added with 4 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 3-methoxymethoxy-4-methylbenzoic acid (2.69 g).

1. customThe solvent was evaporated under reduced pressure
2. dissolutionThe residue was dissolved in methanol (50 mL)
3. additionthe solution was treated with 2 mol/L aqueous potassium hydroxide solution (50 mL)
4. customThe solvent was evaporated under reduced pressure
5. additionThe residue was added with 4 mol/L hydrochloric acid
6. extractionextracted with ethyl acetate
7. washThe organic layer was washed with saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. customThe solvent was evaporated under reduced pressure

ORD record

ord-153c8715831046a0960329654ff08d74

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745641B2