Methanol → Methyl o-toluate

To a stirred solution of 40.0 grams (0.29 mole) of 2-methylbenzoic acid in 200 ml of methanol was added dropwise 20 ml of concentrated sulfuric acid. Upon completion of addition the reaction mixture was heated to reflux where it stirred for 18 hours. The reaction mixture was cooled to ambient temperature and poured into 200 ml of water. The mixture was extracted with three 100 ml portions of methylene chloride. The combined extracts were washed with two 50 ml portions of aqueous saturated sodium bicarbonate solution, then with 50 ml of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 42.7 grams of methyl 2-methylbenzoate.

1. additionUpon completion of addition the reaction mixture
2. temperaturewas heated
3. temperatureto reflux where it
4. extractionThe mixture was extracted with three 100 ml portions of methylene chloride
5. washThe combined extracts were washed with two 50 ml portions of aqueous saturated sodium bicarbonate solution
6. dry with materialThe organic layer was dried with sodium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-0c23a2ff3c9b47be8234dfb8eec38c7c

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04552585