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

HRID 55746Notes

Reaction equation

HRID 55746 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>[Cl:9][C:7](=[O:8])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:10]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 65578Oxalyl chloride

Product 1

HCID 11126621tert-Butyl 2-chloro-2-oxoacetateYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butanol (574 μL, 6.0 mmol) was added to a solution of oxalyl chloride (772 μL, 9.0 mmol) in DCM (3 mL) at 0° C., and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was then concentrated in vacuo to yield t-butyl 2-chloro-2-oxoacetate (403 mg) as a clear colorless liquid. The liquid was dissolved in DCM (2.5 mL) to prepare a 1.0 M solution in DCM.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-665e0d162c7b44beac15bf845ebee58f
Source dataset
uspto-grants-2016_09
Patent number
US09433598B2

Reaction notes

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