1-Butanol → Butyl chloromethyl carbonate
Reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].Cl[C:7]([O:9][CH2:10][Cl:11])=[O:8].N1C=CC=CC=1>C(OCC)C>[C:7](=[O:8])([O:9][CH2:10][Cl:11])[O:5][CH2:1][CH2:2][CH2:3][CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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%).
Workup
- stirringThe solution was stirred at 0° C. for 15 min
- stirringstirred for three additional hours
- filtrationThe ether solution was filtered
- washwashed with 1 M HCl
- dry with materialtwice with water, dried over MgSO4
- filtrationfiltered
- concentrationconcentrated on a rotary evaporator
Sources & evidence
- ORD record
- ord-4a08ef4ee5064e45a7ea63beb414c928
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977089
Reaction notes
Loading…