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 then 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, and then allowed to warm to room temperature where it stirred for 4 hours. After this time, the reaction was cooled to 0° C. and then 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 diluted bleach to remove residual methyl sulfide, 3× with saturated sodium carbonate to remove any unreacted acid, 1× with water, 1× with brine, dried over sodium sulfate and then concentrated in vacuo to yield the methyl 3-(hydroxymethyl)benzoate (845 mg, 5.09 mmol, 87% yield) as a colorless oil.

1. customto exceed 5° C
2. temperatureto warm to room temperature where it
3. stirringstirred for 4 hours
4. temperatureAfter this time, the 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 diluted bleach
10. customto remove residual methyl sulfide, 3× with saturated sodium carbonate
11. customto remove any unreacted acid, 1× with water, 1× with brine
12. dry with materialdried over sodium sulfate
13. concentrationconcentrated in vacuo

ORD record

ord-d442cac5471b4514803e68607e5d6b2e

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536198B2