Structure of 170737-95-8
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CAS No. : | 170737-95-8 |
Formula : | C9H9ClO3 |
M.W : | 200.62 |
SMILES Code : | O=C(O)CC1=CC=C(Cl)C=C1OC |
MDL No. : | MFCD09925126 |
Boiling Point : | No data available |
InChI Key : | UXJIWCMQVOEXTG-UHFFFAOYSA-N |
Pubchem ID : | 14675568 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
With potassium hydroxide; In ethylene glycol; | Example (XVIII-2) (4-Chloro-2-methoxyphenyl)acetic acid 141 g of 4-chloro-2-methoxyphenylacetonitrile are reacted with 83.2 g of potassium hydroxide in 280 ml of ethylene glycol. 148 g of solid are obtained (m.p.: 100 C.). 1H NMR (CDCl3): 8.40-8.90 (m br, 1H); 7.10 (d, 1H); 6.86 (dd, 1H); 6.89 (d, 1H); 3.80 (s, 3H); 3.60 (s, 2H). | |
With potassium hydroxide; water; for 24h;Heating / reflux; | A solution of 4-chloro-2-methoxy-benzyl alcohol (4g) and thionyl chloride (10ml) indichloromethane (30ml) was refluxed for Ih. The solution was concentrated under reducedpressure and the residue partitioned between diethyl ether and water. The organics were driedand evaporated under reduced pressure. This residue and sodium cyanide (Ig) in DMF (20ml)was stirred at room temperature for 3h. The mixture was partitioned between diethyl ether andwater, the organics were dried and evaporated under reduced pressure. A solution ofpotassium hydroxide was added to the residue and the mixture heated under reflux for 24h.The mixture was partitioned between diethyl ether and water, the aqueous layer was acidifiedwith 2M hydrochloric acid and extracted with ethyl acetate. The organic layer was dried andevaporated under reduced pressure. The residue was triturated with diethyl ether andisohexane. Yield 1.4g.1HNMRCDC13: 5 7.11 (1H, d), 6.92 (1H, d), 6.87 (1H, s), 3.82 (3H, s), 3.62 (2H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen bromide; In acetic acid; for 48h;Heating / reflux; | 4-chloro-2-methoxy-benzeneacetic acid (1.4g), HBr (25ml), acetic acid (5ml) wererefluxed for 48h then evaporated under reduced pressure. The residue was azeotroped withtoluene and triturated with diethyl ether and isohexane. Yield 0.56g.1HNMR CDC13: 5 7.12 (1H, d), 6.81-6.76 (2H, m), 3.45 (2H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.5 g | With thionyl chloride; at 60℃; | 2-(4-Chloro-2-methoxyphenyl)acetic acid [CAS 170737-95-8] (5.8 g, 28.9 mmol) was added in small portions to thionyl chloride (50 ml_) and the resulting solution was stirred overnight at 60C. The solvent was concentrated under reduced pressure and co-evaporated with toluene to give 2-(4-chloro-2- methoxyphenyl)acetyl chloride 1a (6.5 g) as an oily residue that was used without further purification in the next step. |
With sulfuryl dichloride; at 60℃; for 16h; | 2-(4-Chloro-2-methoxyphenyl)acetic acid [CAS 170737-95-8] (5.8 g, 28.9 mmol) was added in small portions to thionyl chloride (50 mL) and the resulting solution was stirred overnight at 60C. The solvent was concentrated under reduced pressure and co-evaporated with toluene to give 2-(4-chloro-2-methoxyphenyl)- acetyl chloride 1a (6.5 g) as an oily residue that was used without further purification in the next step. | |
With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 0 - 20℃; for 0.5h; | Synthesis of intermediate 1a: A solution of <strong>[170737-95-8]2-(4-chloro-2-methoxyphenyl)acetic acid</strong> [CAS 170737-95-8] (20 g, 101 mmol) in dry THF (300 ml_) was cooled at 0C. Oxalyl chloride (18 ml_, 202 mmol) and two drops of DMF were added. The reaction mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (300 ml_) and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure to give ethyl 2-(4-chloro-2- methoxyphenyl)acetate 1a (23 g), which was used in the next step without further purification. |
6.5 g | With thionyl chloride; at 60℃; | 2-(4-Chloro-2-methoxyphenyl)acetic acid [CAS 170737-95-8] (5.8 g, 28.9 mmol) was added in small portions to thionyl chloride (50 mL) and the resulting solution was stirred overnight at 6000. The solvent was concentrated under reducedpressure and co-evaporated with toluene to give 2-(4-chloro-2-methoxyphenyl)- acetyl chloride 9a’ (6.5 g) as an oily residue that was used without furtherpurification in the next step. |
With thionyl chloride; at 60℃; | 2-(4-Chloro-2-methoxyphenyl)acetic acid [CAS 170737-95-8] (5.8 g, 28.9 mmol) was added in small portions to thionyl chloride (50 mL) and the resulting solutionwas stirred overnight at 6000. The solvent was concentrated under reduced pressure and co-evaporated with toluene to give 2-(4-chloro-2-methoxyphenyl)- acetyl chloride 9a’ (6.5 g) as an oily residue that was used without further purification in the next step. |
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