Potassium Carbonate → 2-Chloro-3-neopentyloxy-6-nitrotoluene

HRID 1899002Notes

Reaction equation

HRID 1899002 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[OH:12].[CH2:13](I)[C:14]([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[Cl:1][C:2]1[C:3]([O:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 131473552-Chloro-3-methyl-4-nitrophenol

Product 1

HCID 233730942-Chloro-3-neopentyloxy-6-nitrotolueneYield 78.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Reaction of 2-chloro-3-methyl-4-nitrophenol (2.26 g) with neopentyl iodide (4.78 g) in 1-methyl 2-pyrrolidinone (30 ml) in the presence of potassium carbonate (3.34 g) was conducted at 140° C. overnight. The crude product was partitioned between 2M HCl and ethyl acetate, and the organic phase was washed with water, dried (MgSO4) and evaporated to dryness. The residue was chromatographed (SiO2 ; hexane/ether) to give 2-chloro-3-neopentyloxy-6-nitrotoluene as a yellow solid (2.44 g).

Workup

  1. customThe crude product was partitioned between 2M HCl and ethyl acetate
  2. washthe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was chromatographed (SiO2 ; hexane/ether)

Sources & evidence

ORD record
ord-0aeb5653596e4a4abdb41dda6fe420e8
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

Loading…