1,2-Dichloroethane → Carbonic acid, chloromethyl phenyl ester

HRID 745034Notes

Reaction equation

HRID 745034 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].N1C=CC=CC=1.C=[O:18].ClC[CH2:21][Cl:22]>>[C:2](=[O:18])([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[O:3][CH2:21][Cl:22]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 1049PyridineHCID 15891Phenyl chloroformate

Product 1

HCID 14787053Carbonic acid, chloromethyl phenyl ester

Conditions

Temperature
65 °C

Procedure

Phenyl chloroformate (9.0 g, 57.5 mmol) was dissolved in 1,2-dichloroethane (50 ml) and pyridine (0.22 g, 2.8 mmol) was added dropwise to the stirred solution. In another reactor, paraformaldehyde (7.0 g, 233.1 mmol) was heated with a heat gun to generate the gaseous monomer. The formaldehyde gas was bubbled into the first reactor through a tube with the outlet below the surface of the liquid. Stirred at 65° C. for 3 hours. Washed three times with water, dried (MgSO4) and concentrated. Distillation (Bp. 64°-67° C. 5×10-4 mbar) yielded 2.7 g product. The product was further purified by flash chromatography (Silikagel 60, petroleum ether/ethyl acetate 95: 5). Yield: 2.1 g. 1H-NMR (CDCl3): delta=5.78 (CH2); 7.18-7.41 ppm (phenyl).

Workup

  1. customThe formaldehyde gas was bubbled into the first reactor through a tube with the outlet below the surface of the liquid
  2. washWashed three times with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. distillationDistillation (Bp. 64°-67° C. 5×10-4 mbar)

Sources & evidence

ORD record
ord-b551ab794ff849a082fc2f91229e3f02
Source dataset
uspto-grants-1996_09
Patent number
US05559266

Reaction notes

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