Hydrochloric Acid → 5-Bromo-2-(methoxymethoxy)benzaldehyde
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][O:19][CH3:20].Cl>O.CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:18][O:19][CH3:20])=[C:6]([CH:9]=1)[CH:7]=[O:8]Participants
Procedure
To 600 ml of acetone solution containing 30.0 g (0.15 mol) of 5-bromo-2-hydroxybenzaldehyde was added 20.6 g (0.15 mol) of potassium carbonate, and then, 12.5 ml (0.17 mol) of chloromethylmethyl ether was added dropwise to the mixture over 30 minutes under ice-cooling. After stirring the mixture at the same temperature for 30 minutes, the mixture was further stirred at room temperature for 5 hours. After completion of the reaction, 600 ml of water was added to the reaction mixture. A pH of the mixture was adjusted to 7.6 with conc. hydrochloric acid, and extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 28.4 g of the title compound as a pale yellowish oil. (Yield: 77%)
Workup
- temperaturecooling
- stirringthe mixture was further stirred at room temperature for 5 hours
- additionwas added to the reaction mixture
- extractionextracted with ethyl acetate
- customThe organic layer after separation
- washwas washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d6b13c38416d40baa3447b7f442b91b5
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450319B2
Reaction notes
Loading…