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CAS No. : | 3964-57-6 | MDL No. : | MFCD00016418 |
Formula : | C8H7ClO3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ZSBIMTDWIGWJPW-UHFFFAOYSA-N |
M.W : | 186.59 | Pubchem ID : | 77580 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | [00351j Step 1: methyl 3-chloro-4-(2-hydroxy-2-methylpropoxy)benzoate [00352j A 500 ml 3 neck RB flask was fitted with a mechanical stirrer,a J-Kem temperature probe/controller, an addition funnel, a water cooled reflux condenser and a nitrogen inlet/outlet. The vessel was charged under a nitrogen atmosphere with methyl 3-chloro-4-hydroxy-benzoate (10 g, 53.6 mmol) and methylalcohol (40 ml) which provided a clear pale yellow solution. Stirring was commenced and the pot temperature was recorded at 19 °C. The vessel was then charged with potassium carbonate (30 g, 0.21 mol) added as a solid in one portion which resulted in an exotherm to 23 °C. Note: The potassium carbonate was ground to a fine powder prior to use. The resulting suspension was continued to stir at rt for 15 mm and thentreated with 1-chloro-2-methyl-propan-2-ol (11.6 g, 0.11 mol) added neat dropwise via addition funnel over 10 mm. The resulting reaction mixture/suspension was then heated to 70 °C and stirred for 20 h. The reaction mixture was cooled to rt and diluted with ethyl acetate (250 ml). The mixture was filtered through a glass fit Buchner funnel with a 10 mm layer of Celite. The filter cake was washed with ethyl acetate (2 x100 ml). The filtrate was transferred to a separatory funnel and partitioned with 1 M aqueous NaOH (250 ml). The organic was removed and washed with 1 M aqueous NaOH (2 x 150 ml), saturated aqueous sodium chloride (150 ml), dried over sodium sulfate (250 g) and filtered through a glass frit Buchner funnel. The filtrate was concentrated under reduced pressure to provide methyl 3-chloro-4-(2-hydroxy-2-methylpropoxy)benzoate (9.0 g, 65percent) as a clear pale yellow oil. The material was used without further purification in the next synthetic step. ESI-MS mlz caic. 258.7, found 259.2 (M+1) Retention time: 1.46 mm (3 mm run). |
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