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

HRID 381309

Reaction equation

HRID 381309 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[C:14](O)([CH3:17])([CH3:16])[CH3:15].Cl.CN(C)CCCN=C=NCC.C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[C:14]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:12]([CH3:13])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 73194-Methyl-3-nitrobenzoic acidHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22451886Tert-butyl 4-methyl-3-nitrobenzoateYield 99.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-nitro-4-methylbenzoic acid (17.3 g 96 mmol) in dichloromethane (250 ml) and tert-butanol (35.8 g 470 mmol) at 0° C. under nitrogen was added 4-dimethylaminopyridine (6 g 50 mmol) and 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (25.8 g 140 mmol) and the solution allowed to come to room temperature over 1 hour. then stirred overnight. The solution was poured into 1:1 ethyl acetate:water (800 ml) and the organic layer washed with aqueous bicarbonate and saturated aqueous sodium chloride. then dried (MgSO4) and evaporated. to give the product as a clear oil (22.6 g).

Workup

  1. washwater (800 ml) and the organic layer washed with aqueous bicarbonate and saturated aqueous sodium chloride
  2. dry with materialthen dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-5954dda2b21e4891a6aa88f0d3e45ef0
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Linked notes

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