Acetyl chloride → Methyl 3-hydroxy-2-methylbenzoate

Temperature

0 °C

3-Hydroxy-2-methylbenzoic acid (0.5 g, 3.2 mmol) was dissolved in HPLC grade methanol (5 ml) and cooled to 0° C. under nitrogen. Acetyl chloride (5 ml) was added dropwise. Once the addition was complete, the ice bath was removed and the reaction mixture allowed warming to room temperature over a period of 18 hours. The reaction was complete by tlc (Rf=0.5, 1:1 ethyl acetate/hexanes) and quenched with saturated sodium bicarbonate. The reaction mixture was concentrated, diluted with dichloromethane and water and the layers separated. The aqueous layer was extracted with dichloromethane (3×). The organic layers were combined, dried (MgSO4), filtered and concentrated in vacuo, which afforded 0.5 g (91%) of 3-hydroxy-2-methylbenzoic acid methyl ester as a solid.

1. additionOnce the addition
2. customthe ice bath was removed
3. temperaturethe reaction mixture allowed warming to room temperature over a period of 18 hours
4. customquenched with saturated sodium bicarbonate
5. concentrationThe reaction mixture was concentrated
6. additiondiluted with dichloromethane and water
7. customthe layers separated
8. extractionThe aqueous layer was extracted with dichloromethane (3×)
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo, which

ORD record

ord-96a92fee2c6c4be6b581ed58ea3a1b60

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115624B1