Methanol → Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

Into a 3-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-hydroxy-3-methylbenzoic acid (50 g, 328.63 mmol, 1.00 equiv) and methanol (800 mL). This was followed by the addition of thionyl chloride (20 mL) dropwise with stirring. The resulting solution was stirred overnight at 80° C. The resulting mixture was concentrated under vacuum. The residue was diluted with 1000 mL of ethyl acetate. The resulting mixture was washed with 2×800 mL of NaOH (cold). The resulting mixture was washed with 2×500 mL of water. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 25 g (46%) of methyl 2-hydroxy-3-methylbenzoate as brown oil. 1H NMR (300 MHz, DMSO-d6) δ 2.19 (s, 3H), 3.90 (s, 3H), 6.83-6.88 (m, 1H), 7.41-7.44 (m, 1H), 7.64-7.66 (m, 1H), 10.87 (b, 1H).

1. customInto a 3-L 4-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe resulting solution was stirred overnight at 80° C
4. concentrationThe resulting mixture was concentrated under vacuum
5. additionThe residue was diluted with 1000 mL of ethyl acetate
6. washThe resulting mixture was washed with 2×800 mL of NaOH (cold)
7. washThe resulting mixture was washed with 2×500 mL of water
8. dry with materialThe mixture was dried over anhydrous sodium sulfate
9. concentrationconcentrated under vacuum
10. customThis resulted in 25 g (46%) of methyl 2-hydroxy-3-methylbenzoate as brown oil

ORD record

ord-61afc531f8de4c359202dfd864b39f94

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193707B2