Water → Methyl 4-formyl-3-methoxybenzoate

HRID 1009915Notes

Reaction equation

Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14].C(=O)([O-])[OH:16].[Na+].O>CS(C)=O>[CH:2]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])=[O:16]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-(bromomethyl)-3-methoxybenzoate (3.00 g, 11.6 mmol) in dimethyl sulfoxide (16 ml) was added sodium hydrogen carbonate (1.00 g, 13.6 mmol), and the mixture was stirred at 50° C. for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgSO4 and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (1:0-7:3, v/v) to give the title compound (870 mg, 39%) as a colorless oil.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous MgSO4
customthe solvent was evaporated under reduced pressure
washeluted with hexane-ethyl acetate (1:0-7:3

Sources & evidence

ORD record: ord-c472da74d97b44318b15c7f0203f8451
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973163B2

Reaction notes

Loading…