1-Butanol → Butyl chloromethyl carbonate

HRID 1600581Notes

Reaction equation

HRID 1600581 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

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

  1. stirringThe solution was stirred at 0° C. for 15 min
  2. stirringstirred for three additional hours
  3. filtrationThe ether solution was filtered
  4. washwashed with 1 M HCl
  5. dry with materialtwice with water, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-4a08ef4ee5064e45a7ea63beb414c928
Source dataset
uspto-grants-1999_11
Patent number
US05977089

Reaction notes

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