tert-Butanol → tert-Butyl 2-chloro-2-oxoacetate

HRID 1397641Notes

Reaction equation

HRID 1397641 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[C:6](Cl)(=[O:10])[C:7]([Cl:9])=[O:8]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:10])[C:7]([Cl:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 65578Oxalyl chloride

Product 1

HCID 11126621tert-Butyl 2-chloro-2-oxoacetateYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butanol (765 μL, 8.0 mmol) was added dropwise to a solution of oxalyl dichloride (1.0 mL, 12.0 mmol) in DCM (5 mL) at 0° C. The mixture was stirred at room temperature for 1 hour then concentrated in vacuo to yield chloro-oxo-acetic acid t-butyl ester as a clear colorless liquid (1.1 g). A 1 M solution in DCM was prepared by dissolving the liquid (1.1 g, 6.7 mmol) in DCM (6.7 mL).

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-15d26780075543d19713be0c197e983f
Source dataset
uspto-grants-2014_12
Patent number
US08901169B2

Reaction notes

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