1,2-Dichloroethane → 1-Chloro-1-phenylmethyl phenyl carbonate

HRID 745040Notes

Reaction equation

Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1.[Cl:25]CCCl>>[C:2](=[O:3])([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[O:18][CH:11]([Cl:25])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 240Benzaldehyde

HCID 1049Pyridine

HCID 15891Phenyl chloroformate

Product 1

HCID 542165221-Chloro-1-phenylmethyl phenyl carbonate

Conditions

Temperature: 100 °C

Procedure

Phenyl chloroformate (3.0 g, 19.2 mmol) and benzaldehyde (2.4 g, 23.0 mmol) were dissolved in 1,2-dichloroethane (15 ml) and pyridine (0.09 g, 1.14 mmol) was added dropwise to the stirred solution. Stirred at 80° C. for two days and at 100° C. for one day. Washed with water (25 ml), the aqueous phase was back-extracted with dichloromethane (25 ml). The combined organic phases were dried (MgSO4) and concentrated. Purified by flash chromatography (Silikagel 60, petroleum ether/ethyl acetate 95 5). Yield: 1.5 g. 1H-NMR (CDCl3): delta=7.34 (CH); 7.20-7.61 ppm (phenyl). GC/MS: 262.1 (M+).

Workup

washWashed with water (25 ml)
extractionthe aqueous phase was back-extracted with dichloromethane (25 ml)
dry with materialThe combined organic phases were dried (MgSO4)
concentrationconcentrated
customPurified by flash chromatography (Silikagel 60, petroleum ether/ethyl acetate 95 5)

Sources & evidence

ORD record: ord-a9cafde1100d4ce28b8a2d7993424a3d
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559266

Reaction notes

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