3-(Methoxycarbonyl)benzoic acid → Benzoic acid, 3-(hydroxymethyl)-, methyl ester

Temperature

0 °C

A solution of 3-(methoxycarbonyl)benzoic acid (1.05 g, 5.83 mmol) in THF (25 mL) was cooled to 0° C., and treated with the dropwise addition of 2.0 M borane-methylsulfide complex in THF (14.57 mL, 29.1 mmol) at a rate which did not allow the temperature to exceed 5° C. The mixture was stirred at 0° C. for 15 minutes, then allowed to warm to room temperature and stirred for 4 hours. The reaction was cooled to 0° C. and quenched with the addition of small pieces of ice, causing vigorous gas evolution. When gas evolution had ceased, the mixture was diluted with brine and extracted 3× with ethyl acetate. The combined organic phases were washed 3× with dilute bleach to remove residual methyl sulfide, 3× with saturated sodium carbonate to remove any unreacted acid, 1× with water, and 1× with brine, then dried over sodium sulfate and concentrated in vacuo to yield the title compound (845 mg, 5.09 mmol, 87% yield) as a colorless oil.

1. customto exceed 5° C
2. temperatureto warm to room temperature
3. stirringstirred for 4 hours
4. temperatureThe reaction was cooled to 0° C.
5. customquenched with the addition of small pieces of ice
6. additionthe mixture was diluted with brine
7. extractionextracted 3× with ethyl acetate
8. washThe combined organic phases were washed 3×
9. additionwith dilute bleach
10. customto remove residual methyl sulfide, 3× with saturated sodium carbonate
11. customto remove any unreacted acid, 1× with water, and 1× with brine
12. dry with materialdried over sodium sulfate
13. concentrationconcentrated in vacuo

ORD record

ord-f8290a5193d64234a1f4224c4318362f

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985861B2