Potassium Carbonate → 3-(methoxymethyl)benzoic Acid

To a stirred solution of 3-(chloromethyl)benzoate (25.5 g, 138.1 mmol) in methanol (150 mL) at room temperature was added potassium carbonate (95.4 g, 691 mmol). The resulting suspension mixture was stirred 24 h at room temperature, then 4 h at 50° C. After cooling down to room temperature, the insolubles were filtered off, the filtrate concentrated in vacuo and diluted with dichloromethane (500 mL), and extracted with water (250 mL). The aqueous phase was acidified with aq. HCl (1 M) to pH=4 and extracted with dichloromethane (3×300 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to afford 3-(methoxymethyl)benzoic acid as a colourless solid [20.9 g, yield 91%; HPLC/MS:m/z=165 (M−H); log P(HCOOH)=1.33].

1. custom4 h
2. customat 50° C
3. temperatureAfter cooling down to room temperature
4. filtrationthe insolubles were filtered off
5. concentrationthe filtrate concentrated in vacuo
6. additiondiluted with dichloromethane (500 mL)
7. extractionextracted with water (250 mL)
8. extractionextracted with dichloromethane (3×300 mL)
9. dry with materialThe combined organic layers were dried (MgSO4)
10. concentrationconcentrated in vacuo

ORD record

ord-b31cc4fba7314c8d9968ec090a91a6b4

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492388B2