No renderable structure data available
CC1=CC=C(C=C1)S(=O)(=O)OC(=O)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | (4-methylphenyl)sulfonyl acetate |
|---|---|
| IUPAC Name | — |
| CAS Number | 26908-82-7 |
| Database ID | 292480 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
(4-methylphenyl)sulfonyl acetate (CAS 26908-82-7) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 292480
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
9 reactions · 9 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6f7df138c2d54f23b4c17c5196d1cc02Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 7 (10 g, 40 mmol, 1 equiv) and pyridine (22.6 mL, 280 mmol, 7 equiv) in dichloromethane (200 mL) was added p-toluenesulfonyl chloride (11.4 g, 60 mmol, 1.5 equiv). The mixture stirred at room temperature overnight. Pyridine (22.6 mL, 280 mmol, 7 equiv) and acetic anhydride (21.9 mL, 232 mmol, 5.8 equiv) were added at room temperature and the mixture was stirred overnight. The reaction was cooled to 5° C. and quenched with 2 N aq NaOH to pH 7. The aqueous layer was separated and extracted with dichloromethane (2×50 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated. The resulting semi-solid was dissolved in isopropyl acetate (100 mL) and concentrated to dryness. This was repeated 2 more times. The resulting semi-solid was triturated in methyl tert-butyl ether (250 mL), filtered and dried under vacuum to afford 8.1 g of 8 (45%) as a pale yellow solid. the mixture was stirred overnight The reaction was cooled to 5° C. quenched with 2 N aq NaOH to pH 7 The aqueous layer was separated extracted with dichloromethane (2×50 mL) The combined organics were dried over sodium sulfate filtered concentrated The resulting semi-solid was dissolved in isopropyl acetate (100 mL) concentrated to dryness The resulting semi-solid was triturated in methyl tert-butyl ether (250 mL) filtered dried under vacuum
Source ID: ord-366fbad9cd6c4f22a2923d8a3a342e78Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 7 (10 g, 40 mmol, 1 equiv) and pyridine (22.6 mL, 280 mmol, 7 equiv) in dichloromethane (200 mL) was added p-toluenesulfonyl chloride (11.4 g, 60 mmol, 1.5 equiv). The mixture stirred at room temperature overnight. Pyridine (22.6 mL, 280 mmol, 7 equiv) and acetic anhydride (21.9 mL, 232 mmol, 5.8 equiv) were added at room temperature and the mixture was stirred overnight. The reaction was cooled to 5° C. and quenched with 2 N aq NaOH to pH 7. The aqueous layer was separated and extracted with dichloromethane (2×50 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated. The resulting semi-solid was dissolved in isopropyl acetate (100 mL) and concentrated to dryness. This was repeated 2 more times. The resulting semi-solid was triturated in methyl tert-butyl ether (250 mL), filtered and dried under vacuum to afford 8.1 g of 8 (45%) as a pale yellow solid. the mixture was stirred overnight The reaction was cooled to 5° C. quenched with 2 N aq NaOH to pH 7 The aqueous layer was separated extracted with dichloromethane (2×50 mL) The combined organics were dried over sodium sulfate filtered concentrated The resulting semi-solid was dissolved in isopropyl acetate (100 mL) concentrated to dryness The resulting semi-solid was triturated in methyl tert-butyl ether (250 mL) filtered dried under vacuum
Source ID: ord-366fbad9cd6c4f22a2923d8a3a342e78Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 7 (10 g, 40 mmol, 1 equiv) and pyridine (22.6 mL, 280 mmol, 7 equiv) in dichloromethane (200 mL) was added p-toluenesulfonyl chloride (11.4 g, 60 mmol, 1.5 equiv). The mixture stirred at room temperature overnight. Pyridine (22.6 mL, 280 mmol, 7 equiv) and acetic anhydride (21.9 mL, 232 mmol, 5.8 equiv) were added at room temperature and the mixture was stirred overnight. The reaction was cooled to 5° C. and quenched with 2 N aq NaOH to pH 7. The aqueous layer was separated and extracted with dichloromethane (2×50 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated. The resulting semi-solid was dissolved in isopropyl acetate (100 mL) and concentrated to dryness. This was repeated 2 more times. The resulting semi-solid was triturated in methyl tert-butyl ether (250 mL), filtered and dried under vacuum to afford 8.1 g of 8 (45%) as a pale yellow solid. the mixture was stirred overnight The reaction was cooled to 5° C. quenched with 2 N aq NaOH to pH 7 The aqueous layer was separated extracted with dichloromethane (2×50 mL) The combined organics were dried over sodium sulfate filtered concentrated The resulting semi-solid was dissolved in isopropyl acetate (100 mL) concentrated to dryness The resulting semi-solid was triturated in methyl tert-butyl ether (250 mL) filtered dried under vacuum
Source ID: ord-366fbad9cd6c4f22a2923d8a3a342e78Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To the acetic p-toluenesulfonic anhydride obtained above was then added at room temperature 100 ml. (1.13 mole) of dimethoxymethane. The temperature of the reaction rose to 38° C. within about 5 minutes. The reaction mixture was stirred for one hour. NMR analysis indicated the title product was obtained in 90% purity after removal of excess dimethoxymethane by stripping at room temperature. was then added at room temperature 100 ml
Source ID: ord-68eb7abfee434af99d9a4eb95f930d1bConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Acetyl chloride (100 ml.; density=1.104 g./ml.) was charged into a suitable reaction flask containing 30 g. (0.158 mole) p-toluenesulfonic acid monohydrate. Vigorous evolution of HCl gas occurred immediately. An efficient HCl trap was attached to the reaction system. The reaction mixture was then heated to mild reflux (~55° C.) and was held to this temperature for 25 minutes. Heating was stopped and the reaction mixture allowed to drop to room temperature over 10-20 minutes with stirring. Vacuum (~20-50 mm) was applied cautiously to remove acetyl chloride without carryover. At the same time the mixture was heated gradually to 60° C. Distillation of acetyl chloride was complete in ~30 minutes with collection in an ice cold flask for reuse. The oil obtained was then subjected to vacuum (~5-10 mm) to remove the last traces of acetyl chloride and acetic acid at 37° C. A snow white solid then crystallized in about 30 minutes as the title product. containing 30 g An efficient HCl trap was attached to the reaction system The reaction mixture was then heated to mild reflux (~55° C.) Heating to drop to room temperature over 10-20 minutes to remove acetyl chloride without carryover Distillation of acetyl chloride was complete in ~30 minutes with collection in an ice cold flask for reuse The oil obtained to remove the last traces of acetyl chloride and acetic acid at 37° C A snow white solid then crystallized in about 30 minutes as the title product
Source ID: ord-826bfd8dc613490ba7469a12f952c723Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To the acetic p-toluenesulfonic anhydride obtained above was then added at room temperature 100 ml. (1.13 mole) of dimethoxymethane. The temperature of the reaction rose to 38° C. within about 5 minutes. The reaction mixture was stirred for one hour. NMR analysis indicated the title product was obtained in 90% purity after removal of excess dimethoxymethane by stripping at room temperature. was then added at room temperature 100 ml
Source ID: ord-4fb24187e93143f29bc8b1657ca7cd6fConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Acetyl chloride (100 ml.; density=1.104 g./ml.) was charged into a suitable reaction flask containing 30 g. (0.158 mole) p-toluenesulfonic acid monohydrate. Vigorous evolution of HCl gas occurred immediately. An efficient HCl trap was attached to the reaction system. The reaction mixture was then heated to mild reflux (~55° C.) and was held to this temperature for 25 minutes. Heating was stopped and the reaction mixture allowed to drop to room temperature over 10-20 minutes with stirring. Vacuum (~20-50 mm) was applied cautiously to remove acetyl chloride without carryover. At the same time the mixture was heated gradually to 60° C. Distillation of acetyl chloride was complete in ~30 minutes with collection in an ice cold flask for reuse. The oil obtained was then subjected to vacuum (~5-10 mm) to remove the last traces of acetyl chloride and acetic acid at 37° C. A snow white solid then crystallized in about 30 minutes as the title product. containing 30 g An efficient HCl trap was attached to the reaction system The reaction mixture was then heated to mild reflux (~55° C.) Heating to drop to room temperature over 10-20 minutes to remove acetyl chloride without carryover Distillation of acetyl chloride was complete in ~30 minutes with collection in an ice cold flask for reuse The oil obtained to remove the last traces of acetyl chloride and acetic acid at 37° C A snow white solid then crystallized in about 30 minutes as the title product
Source ID: ord-28c9b638db4f462a9494ae3d17617c2aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 7 (10 g, 40 mmol, 1 equiv) and pyridine (22.6 mL, 280 mmol, 7 equiv) in dichloromethane (200 mL) was added p-toluenesulfonyl chloride (11.4 g, 60 mmol, 1.5 equiv). The mixture stirred at room temperature overnight. Pyridine (22.6 mL, 280 mmol, 7 equiv) and acetic anhydride (21.9 mL, 232 mmol, 5.8 equiv) were added at room temperature and the mixture was stirred overnight. The reaction was cooled to 5° C. and quenched with 2 N aq NaOH to pH 7. The aqueous layer was separated and extracted with dichloromethane (2×50 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated. The resulting semi-solid was dissolved in isopropyl acetate (100 mL) and concentrated to dryness. This was repeated 2 more times. The resulting semi-solid was triturated in methyl tert-butyl ether (250 mL), filtered and dried under vacuum to afford 8.1 g of 8 (45%) as a pale yellow solid. the mixture was stirred overnight The reaction was cooled to 5° C. quenched with 2 N aq NaOH to pH 7 The aqueous layer was separated extracted with dichloromethane (2×50 mL) The combined organics were dried over sodium sulfate filtered concentrated The resulting semi-solid was dissolved in isopropyl acetate (100 mL) concentrated to dryness The resulting semi-solid was triturated in methyl tert-butyl ether (250 mL) filtered dried under vacuum
Source ID: ord-366fbad9cd6c4f22a2923d8a3a342e78PubChem References
These sources are listed in the compound's public database record.
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