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

HRID 1934599

Reaction equation

HRID 1934599 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 each) 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 each) and the organic layer washed with aqueous bicarbonate and saturated aqueous sodium chloride
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-32d11e3a66b0445a982737101d22788b
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Linked notes

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