2-Chloroethyl chloroformate → 2-((1,1-Dimethylethoxy)methyl)oxirane

HRID 1702756Notes

Reaction equation

HRID 1702756 reaction equation
C(=O)(OCCCl)[O:2][CH:3]([CH2:6][O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:4]Cl.C(OCC(O)CCl)(C)(C)C.ClC(OCCCl)=O>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.C(Cl)CCl>[CH2:6]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH:3]1[O:2][CH2:4]1

Participants

6

Reactant 3

HCID 123052-Chloroethyl chloroformateHCID 109208892-Propanol, 1-chloro-3-(1,1-dimethylethoxy)-HCID 20524944HCID 20524944, compound

Product 1

HCID 243142-((1,1-Dimethylethoxy)methyl)oxirane

Reagents, catalysts & solvents 2

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Following the procedure of Example 14, 3-tert-butoxy-1-chloro-2-propyl 2-chloroethyl carbonate (from the reaction of 3-tert-butoxy-1-chloro-2-propanol with 2-chloroethyl chloroformate) is heated in the presence of tetrabutylphosphonium bromide to produce tert-butyl glycidyl ether and ethylene dichloride as the principal reaction products.

Sources & evidence

ORD record
ord-3d60cc05519a46f88dbcf9299c6c5ae3
Source dataset
uspto-grants-1982_09
Patent number
US04349482

Reaction notes

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