2-Methyl-2-butene → 4-Bromo-2-methoxy-6-methylbenzoic acid

To a suspension of 4-bromo-2-methoxy-6-methyl-benzaldehyde (1.25 g, 5.45 mmol) in tert-butanol (21.7 ml) is added a solution of sodium chlorite (0.98 g, 10.9 mmol) and monosodium phosphate (4.25 g, 27.3 mmol) in water (11 ml). To the solution is added 2-methyl-2-butene (4.63 ml, 43.7 mmol). The resulting homogeneous solution is stirred at RT for 30 min. After completion of the reaction, the solvent is evaporated and the residue is diluted with water and acidified with 1 M hydrochloric acid to pH=1 and extracted with methyl tert-butyl ether (3×40 ml). The combined organic layers are extracted with 1 M sodium hydroxide solution which is further acidified with 6 M hydrochloric acid and extracted with ethyl acetate (3×50 ml). The organic layer is washed with brine (40 ml), dried over sodium sulfate and concentrated to yield 4-bromo-2-methoxy-6-methyl-benzoic acid (1.2 g, 4.89 mmol, 90%).

1. customAfter completion of the reaction
2. customthe solvent is evaporated
3. additionthe residue is diluted with water
4. extractionextracted with methyl tert-butyl ether (3×40 ml)
5. extractionThe combined organic layers are extracted with 1 M sodium hydroxide solution which
6. extractionextracted with ethyl acetate (3×50 ml)
7. washThe organic layer is washed with brine (40 ml)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated

ORD record

ord-59d2fc30d3cf4f7698d9e9e835731d24

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108936B2