No renderable structure data available
CCCCOC(=O)OCClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | butyl chloromethyl carbonate |
|---|---|
| IUPAC Name | — |
| CAS Number | 58304-98-6 |
| Database ID | 15256996 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
butyl chloromethyl carbonate (CAS 58304-98-6) 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 15256996
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5948c214fd6f4630a51d618edf743fbdConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e1bc3786e68049bb855f35e22db1271eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of butyl alcohol (50 mmol) and chloromethyl chloroformate (4.5 mL, 50 mmol) in diethyl ether (200 mL) was cooled to 0° C. under argon. Pyridine (5.7 mL, 50 mmol) was added dropwise with stirring over 5 min. The solution was stirred at 0° C. for 15 min, then allowed to warm to room temperature and stirred for three additional hours. The ether solution was filtered, washed with 1 M HCl, and then twice with water, dried over MgSO4, filtered, and concentrated on a rotary evaporator to give butyl chloromethyl carbonate (7 g, 85%). The solution was stirred at 0° C. for 15 min stirred for three additional hours The ether solution was filtered washed with 1 M HCl twice with water, dried over MgSO4 filtered concentrated on a rotary evaporator
Source ID: ord-0d2f32e9e64b4298a2f31b59981f14b1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of butyl alcohol (50 mmol) and chloromethyl chloroformate (4.5 mL, 50 mmol) in diethyl ether (200 mL) was cooled to 0° C. under argon. Pyridine (5.7 mL, 50 mmol) was added dropwise with stirring over 5 min. The solution was stirred at 0° C. for 15 min, then allowed to warm to room temperature and stirred for three additional hours. The ether solution was filtered, washed with 1 M HCl, and then twice with water, dried over MgSO4, filtered, and concentrated on a rotary evaporator to give butyl chloromethyl carbonate (7 g, 85%). The solution was stirred at 0° C. for 15 min stirred for three additional hours The ether solution was filtered washed with 1 M HCl twice with water, dried over MgSO4 filtered concentrated on a rotary evaporator
Source ID: ord-6da0f8ddde7a4b8798032fd5b90eefddConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of butyl alcohol (50 mmol) and chloromethyl chloroformate (4.5 mL, 50 mmol) in diethyl ether (200 mL) was cooled to 0° C. under argon. Pyridine (5.7 mL, 50 mmol) was added dropwise with stirring over 5 min. The solution was stirred at 0° C. for 15 min, then allowed to warm to room temperature and stirred for three additional hours. The ether solution was filtered, washed with 1 M HCl, and then twice with water, dried over MgSO4, filtered, and concentrated on a rotary evaporator to give butyl chloromethyl carbonate (7 g, 85%). The solution was stirred at 0° C. for 15 min stirred for three additional hours The ether solution was filtered washed with 1 M HCl twice with water, dried over MgSO4 filtered concentrated on a rotary evaporator
Source ID: ord-6da0f8ddde7a4b8798032fd5b90eefddConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium tert. butoxide (5.84 g, 0.052 mol ) was added to a solution of acrylic acid (4.47 g, 0.045 mol) in DMF (220 ml). Butyl chloromethyl carbonate (Example li, 6.5 g, 0.052 mol) in DMF (150 ml) was added to the resulting suspension. 18crown-6 (0.6 g) was then added and the reaction mixture was left with stirring at room temperature for 2 days. The reaction mixture was filtered and the solvent was removed under reduced pressure. The residue was dissolved in chloroform (100 ml) and washed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml). The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. Flash chromatography gave 4.57 g of the title product. the reaction mixture was left The reaction mixture was filtered the solvent was removed under reduced pressure The residue was dissolved in chloroform (100 ml) washed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml) The organic phase was dried (MgSO4) the solvent removed under reduced pressure
Source ID: ord-ef6fa73cccdb4c43a5ead21ec2572a93Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium tert. butoxide (5.84 g, 0.052 mol ) was added to a solution of acrylic acid (4.47 g, 0.045 mol) in DMF (220 ml). Butyl chloromethyl carbonate (Example li, 6.5 g, 0.052 mol) in DMF (150 ml) was added to the resulting suspension. 18crown-6 (0.6 g) was then added and the reaction mixture was left with stirring at room temperature for 2 days. The reaction mixture was filtered and the solvent was removed under reduced pressure. The residue was dissolved in chloroform (100 ml) and washed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml). The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. Flash chromatography gave 4.57 g of the title product. the reaction mixture was left The reaction mixture was filtered the solvent was removed under reduced pressure The residue was dissolved in chloroform (100 ml) washed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml) The organic phase was dried (MgSO4) the solvent removed under reduced pressure
Source ID: ord-ef6fa73cccdb4c43a5ead21ec2572a93Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5948c214fd6f4630a51d618edf743fbdConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e1bc3786e68049bb855f35e22db1271eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium tert. butoxide (5.84 g, 0.052 mol) was added to a solution of acrylic acid (4.47 g, 0.045 mol) in DMF (220 ml). Butyl chloromethyl carbonate (6.5 g, 0.052 mol) in DMF (150 ml) was added to the resulting suspension. 18-crown-6 (0.6 g) was then added and the reaction mixture was left with stirring at room temperature for 2 days. The reaction mixture was filtered and the solvent was removed under reduced pressure. The residue was dissolved in chloroform (100 ml) and washed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml). The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. Flash chromatography gave 4.57 g of the title product. the reaction mixture was left The reaction mixture was filtered the solvent was removed under reduced pressure The residue was dissolved in chloroform (100 ml) washed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml) The organic phase was dried (MgSO4) the solvent removed under reduced pressure
Source ID: ord-0e3620b4f8c44565a27c3be57a956513Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The intermediate n-butyl chloromethyl carbonate (2.5 g 15.0 mmol) was dissolved in dimethyl formamide (80 ml), and potassium methacrylate (1.77 g, 15.0 mmol) was added together with a catalytic amount of 18-crown-6 (0.2 g, 7.5 mmol). After 3 days at 25° C. the solvent was removed under reduced pressure, cholorform (30 ml) and water (20 ml) were added and the product was extracted into chloroform. The solvent was removed under reduced pressure after drying (MgSO4). Flash chromatography gave 1.96 g (61%) of butyl methacryloyloxymethyl carbonate. After 3 days at 25° C. the solvent was removed under reduced pressure, cholorform (30 ml) and water (20 ml) were added the product was extracted into chloroform The solvent was removed under reduced pressure after drying (MgSO4)
Source ID: ord-a8fc3731810343ad979c88a2ef36f72dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of butyl alcohol (50 mmol) and chloromethyl chloroformate (4.5 mL, 50 mmol) in diethyl ether (200 mL) was cooled to 0° C. under argon. Pyridine (5.7 mL, 50 mmol) was added dropwise with stirring over 5 min. The solution was stirred at 0° C. for 15 min, then allowed to warm to room temperature and stirred for three additional hours. The ether solution was filtered, washed with 1 M HCl, and then twice with water, dried over MgSO4, filtered, and concentrated on a rotary evaporator to give butyl chloromethyl carbonate (7 g, 85%). The solution was stirred at 0° C. for 15 min stirred for three additional hours The ether solution was filtered washed with 1 M HCl twice with water, dried over MgSO4 filtered concentrated on a rotary evaporator
Source ID: ord-4a08ef4ee5064e45a7ea63beb414c928PubChem References
These sources are listed in the compound's public database record.
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