tert-Butanol → Tert-butyl 4-chloro-3-nitrobenzoate

HRID 1464437Notes

Reaction equation

HRID 1464437 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17].[C:19]([OH:23])([CH3:22])([CH3:21])[CH3:20]>>[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:12])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 1234774-Chloro-3-nitrobenzoyl chlorideHCID 178418339Butyllithium

Product 1

HCID 10611184Tert-butyl 4-chloro-3-nitrobenzoate

Procedure

A solution of n-butyl lithium (1.6 M, 101 mL) was added dropwise to stirring anhydrous tert-butanol (200 mL) under nitrogen in a room temperature water bath. After 0.5 hours, 4-chloro-3-nitrobenzoyl chloride (10.0 g) was added, and the dark solution was stirred for 1.5 hours at room temperature. The reaction was evaporated under vacuum, and the residue was crystallized from hexane to yield the title compound as an orange solid. Mp: 66°-67° C.

Workup

  1. customThe reaction was evaporated under vacuum
  2. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-82b2baf2a0884caca872d59c1498aaf2
Source dataset
uspto-grants-1994_04
Patent number
US05304644

Reaction notes

Loading…