Diethyl Ether → Benzyl methyl carbonate

HRID 542574Notes

Reaction equation

HRID 542574 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](=[O:14])([O:12]C)[O:10][CH3:11].CN(C)C=O.C(OCC)C>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.O>[C:9](=[O:12])([O:10][CH3:11])[O:14][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 12021Dimethyl Carbonate

Product 1

HCID 11182814Benzyl methyl carbonateYield 65%

Reagents, catalysts & solvents 2

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

Benzyl chloride (31.65 g, 0.25 mole), dimethyl carbonate (90.0 g, 1.0 mole), tetra-n-butylphosphonium bromide (3.39 g, 0.01 mole) and N,N-dimethylformamide (200 ml) are heated to 117° C.-118° C. for 6 hours. After heating is discontinued the reaction mixture is added to 300 ml of diethyl ether and 300 ml of water. The organic layer is washed with 3×100-ml allotments of water followed by 2×100 ml-portions of 10 percent aqueous HCl, 100 ml of saturated aqueous NaHCO3 and 100 ml of a saturated aqueous NaCl solution, and dried over MgSO4. After solvent removal, distillation gives 27.02 g (65 percent yield based on benzyl chloride) of benzyl methyl carbonate, b.p. 110° C.-111° C. (11 torr).

Workup

  1. temperatureAfter heating
  2. washThe organic layer is washed with 3×100-ml allotments of water
  3. dry with materialdried over MgSO4
  4. customAfter solvent removal, distillation

Sources & evidence

ORD record
ord-2e18df7161954e40aed11151acdb878c
Source dataset
uspto-grants-1987_04
Patent number
US04658041

Reaction notes

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