Hydrochloric Acid → Methyl 2-(4-chloromethylphenoxy)propionate
Reaction equation
O[CH2:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.[ClH:16]>>[Cl:16][CH2:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1Participants
Procedure
A mixture of 2.19 g (0.0104 mole) of methyl 2-(4-hydroxymethylphenoxy)propionate and 3.00 g (0.0823 mole) of 36% hydrochloric acid was stirred for fifteen minutes at room temperature. The reaction mixture was then poured into ice-water, and the resulting mixture was extracted with diethyl ether. The extracts were combined and washed in succession with water and a saturated aqueous solution of sodium bicarbonate. The extract was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated from the filtrate under reduced pressure, leaving a colorless liquid. This liquid was placed on a column of silica gel and eluted with methylene chloride. After the product-containing fractions were combined and the solvent evaporated under reduced pressure, 1.6 g of methyl 2-(4-chloromethylphenoxy)propionate was isolated as a colorless liquid. The NMR and IR spectra were consistent with the proposed structure.
Workup
- extractionthe resulting mixture was extracted with diethyl ether
- washwashed in succession with water
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent was evaporated from the filtrate under reduced pressure
- customleaving a colorless liquid
- washeluted with methylene chloride
- customthe solvent evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b9ee0b41f23a4997a8a17d974095e625
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05674810
Reaction notes
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